2-benzhydrylpyrrolidine [2-(diphenylmethyl)pyrrolidine] [CAS 383127-45-5; InChIKey OXOBKZZXZV

Query Query

NH

1. Query

Results

Date

14 substances in Reaxys

2016-03-15 08h:47m:15s (EST)

Search as: As drawn

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

1/16

2016-03-15 08:50:35

Reaxys ID 5939930 View in Reaxys

1/14 CAS Registry Number: 22348-31-8; 119237-64-8 Chemical Name: (S)-(-)-2-(diphenylmethyl)pyrrolidine; (S)-(-)-2diphenylmethyl-pyrrolidine; (S)-2-(diphenylmethyl)pyrrolidine; (S)-2-benzhydrylpyrrolidine; (S)-2-(1,1-diphenyl-methyl)-pyrrolidine; S-(-)-2-(diphenylmethyl)-pyrrolidine; (S)-2-diphenylmethylpyrrolidine Linear Structure Formula: C17H19N Molecular Formula: C17H19N Molecular Weight: 237.345 Type of Substance: heterocyclic InChI Key: OXOBKZZXZVFOBB-INIZCTEOSA-N Note:

H

NH

Substance Label (8) Label References 10

Sciebura, Jacek; Gawronski, Jacek; Tetrahedron Asymmetry; vol. 24; nb. 11; (2013); p. 683 - 688, View in Reaxys

A; B

Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; WO2007/112358; (2007); (A1) English, View in Reaxys

B

Chi, Yonggui; Gellman, Samuel H.; Organic Letters; vol. 7; nb. 19; (2005); p. 4253 - 4256, View in Reaxys

1

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys

28

Ma, Dawei; Xia, Chengfeng; Jiang, Jiqing; Zhang, Jianhua; Tang, Wenjun; Journal of Organic Chemistry; vol. 68; nb. 2; (2003); p. 442 - 451, View in Reaxys

4

Patent; The University of Sheffield; US2003/195366; (2003); (A1) English, View in Reaxys

39

Huang, Xuefei; Fujioka, Naoko; Pescitelli, Gennaro; Koehn, Frank E.; Williamson, R. Thomas; Nakanishi, Koji; Berova, Nina; Journal of the American Chemical Society; vol. 124; nb. 35; (2002); p. 10320 - 10335, View in Reaxys

(S)-7d

Enders, Dieter; Kipphardt, Helmut; Gerdes, Peter; Brena-Valle, Leonardo J.; Bhushan, Vidya; Bulletin des Societes Chimiques Belges; vol. 97; nb. 8-9; (1988); p. 691 - 704, View in Reaxys

Patent-Specific Data (2) References Patent; TAKASAGO INTERNATIONAL CORPORATION; US2010/324338; (2010); (A1) English, View in Reaxys Patent; The University of Sheffield; US2003/195366; (2003); (A1) English, View in Reaxys Derivative (1) Derivative

References

(S)-2-(diphenylBailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb. 1; (1997); p. 149 methyl)pyrrolidine 153, View in Reaxys hydrochloride Boiling Point (1) Boiling Point [°C] 135

Pressure (Boiling Point) [Torr]

References

0.01

Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb.

1; (1997); p. 149 - 153, View in Reaxys

Association (MCS) (2) 1 of 2

Description (Association NMR spectrum of the complex (MCS)) Solvent (Association (MCS))

CDCl3

Temperature (Association (MCS)) [°C]

25

Partner (Association (MCS))

Oxone

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

2/16

2016-03-15 08:50:35

2 of 2

Description (Association IR spectrum of the complex (MCS)) Solvent (Association (MCS))

solid

Partner (Association (MCS))

Oxone

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys Circular Dichroism (1) Comment (Circu- References lar Dichroism) Circular dichroism Sciebura, Jacek; Gawronski, Jacek; Tetrahedron Asymmetry; vol. 24; nb. 11; (2013); p. 683 - 688, given View in Reaxys Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

References Kobayashi, Shoji; Kinoshita, Tatsuhiro; Uehara, Hisatoshi; Sudo, Tomoko; Ryu, Llhyong; Organic Letters; vol. 11; nb. 17; (2009); p. 3934 - 3937, View in Reaxys

Optical Rotatory Power (3) 1 of 3

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.32 g/100ml

Length of Path [cm]

5

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-7.6

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

25

Location

supporting information

Kobayashi, Shoji; Kinoshita, Tatsuhiro; Uehara, Hisatoshi; Sudo, Tomoko; Ryu, Llhyong; Organic Letters; vol.

11; nb. 17; (2009); p. 3934 - 3937, View in Reaxys 2 of 3

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.05 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-7.84

Wavelength (Optical Ro- 589 tatory Power) [nm] Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb. 1; (1997); p. 149 - 153, View in Reaxys 3 of 3

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.1 g/100ml

Solvent (Optical Rotatory Power)

CH2Cl2

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

3/16

2016-03-15 08:50:35

Optical Rotatory Power [deg]

-7.8

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

23

Enders, Dieter; Kipphardt, Helmut; Gerdes, Peter; Brena-Valle, Leonardo J.; Bhushan, Vidya; Bulletin des Societes Chimiques Belges; vol. 97; nb. 8-9; (1988); p. 691 - 704, View in Reaxys NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Kobayashi, Shoji; Kinoshita, Tatsuhiro; Uehara, Hisatoshi; Sudo, Tomoko; Ryu, Llhyong; Organic Letters; vol.

11; nb. 17; (2009); p. 3934 - 3937, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Kobayashi, Shoji; Kinoshita, Tatsuhiro; Uehara, Hisatoshi; Sudo, Tomoko; Ryu, Llhyong; Organic Letters; vol.

11; nb. 17; (2009); p. 3934 - 3937, View in Reaxys 3 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Enders, Dieter; Kipphardt, Helmut; Gerdes, Peter; Brena-Valle, Leonardo J.; Bhushan, Vidya; Bulletin des Societes Chimiques Belges; vol. 97; nb. 8-9; (1988); p. 691 - 704, View in Reaxys; Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb. 1; (1997); p. 149 - 153, View in Reaxys 4 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Enders, Dieter; Kipphardt, Helmut; Gerdes, Peter; Brena-Valle, Leonardo J.; Bhushan, Vidya; Bulletin des Societes Chimiques Belges; vol. 97; nb. 8-9; (1988); p. 691 - 704, View in Reaxys; Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb. 1; (1997); p. 149 - 153, View in Reaxys IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Bands

Location

supporting information

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

4/16

2016-03-15 08:50:35

Comment (IR Spectroscopy)

neat liquid

Kobayashi, Shoji; Kinoshita, Tatsuhiro; Uehara, Hisatoshi; Sudo, Tomoko; Ryu, Llhyong; Organic Letters; vol.

11; nb. 17; (2009); p. 3934 - 3937, View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3405 - 2962 cm**(-1)

Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb. 1; (1997); p. 149 - 153, View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3300 - 700 cm**(-1)

Enders, Dieter; Kipphardt, Helmut; Gerdes, Peter; Brena-Valle, Leonardo J.; Bhushan, Vidya; Bulletin des Societes Chimiques Belges; vol. 97; nb. 8-9; (1988); p. 691 - 704, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) spectrum; chemical ionization (CI)

Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb. 1; (1997); p. 149 153, View in Reaxys

spectrum

Enders, Dieter; Kipphardt, Helmut; Gerdes, Peter; Brena-Valle, Leonardo J.; Bhushan, Vidya; Bulletin des Societes Chimiques Belges; vol. 97; nb. 8-9; (1988); p. 691 - 704, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Absorption Maxima (UV/ 188 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

57000

Sciebura, Jacek; Gawronski, Jacek; Tetrahedron Asymmetry; vol. 24; nb. 11; (2013); p. 683 - 688, View in Reaxys Use (1) Laboratory Use and Handling

References

highly enantiose- Chi, Yonggui; Gellman, Samuel H.; Organic Letters; vol. 7; nb. 19; (2005); p. 4253 - 4256, View in Reaxys lective catalyst for Michael addition of aldehydes to simple enones Quantum Chemical Calculations (2) Calculated Prop- Method (Quantum References erties Chemical Calculations) Population analysis, charge distribution

Ab initio calcns.

(LCAO, GO SCF, DIM, SAMO, X-à, Hartree-Fock)

Sciebura, Jacek; Gawronski, Jacek; Tetrahedron Asymmetry; vol. 24; nb. 11; (2013); p.

683 - 688, View in Reaxys

Circular dichroism Ab initio calcns.

(LCAO, GO SCF, DIM, SAMO, X-à, Hartree-Fock)

Sciebura, Jacek; Gawronski, Jacek; Tetrahedron Asymmetry; vol. 24; nb. 11; (2013); p.

683 - 688, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

5/16

2016-03-15 08:50:35

Reaxys ID 14561425 View in Reaxys

2/14 CAS Registry Number: 22348-31-8 Chemical Name: (R)-2-(diphenylmethyl)pyrrolidine; (R)-2-diphenylmethyl-pyrrolidine Linear Structure Formula: C17H19N Molecular Formula: C17H19N Molecular Weight: 237.345 InChI Key: OXOBKZZXZVFOBB-MRXNPFEDSA-N Note:

NH

Substance Label (3) Label References 3b

Doulcet, Julien; Stephenson, G. Richard; Chemistry - A European Journal; vol. 21; nb. 38; (2015); p. 13431 - 13436, View in Reaxys

C

Shyam, Pranab K.; Jang, Hye-Young; European Journal of Organic Chemistry; vol. 2014; nb. 9; (2014); p.

1817 - 1822, View in Reaxys

2.36

Patent; DSM IP ASSETS B.V.; WO2006/50988; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; TAKASAGO INTERNATIONAL CORPORATION; US2010/324338; (2010); (A1) English, View in Reaxys Catalyst Investigation (1) 1 of 1

Investigated characteris- Catalytic activity; Enantiomeric excess; Diastereomeric excess tic(s) Specification of catalysis Stereoselective catalysis Co-catalyst/co-substrate FeCl3·6H2O; tetrabutyl ammonium fluoride name Shyam, Pranab K.; Jang, Hye-Young; European Journal of Organic Chemistry; vol. 2014; nb. 9; (2014); p. 1817 1822, View in Reaxys

Reaxys ID 1572738 View in Reaxys

3/14 CAS Registry Number: 383127-45-5 Chemical Name: 2-(diphenylmethyl)pyrrolidine; α-(α-Pyrrolidinyl)-diphenylmethan Linear Structure Formula: C17H19N Molecular Formula: C17H19N Molecular Weight: 237.345 Type of Substance: heterocyclic InChI Key: OXOBKZZXZVFOBB-UHFFFAOYSA-N Note:

NH

Substance Label (2) Label References 4

Lovely, Ann E.; Wenzel, Thomas J.; Tetrahedron Asymmetry; vol. 17; nb. 18; (2006); p. 2642 - 2648, View in Reaxys

I

Patent; Roussel-Uclaf; FRM3638; (1964); Chem.Abstr.; vol. 70; nb. 106375m; (1969), View in Reaxys

Derivative (1) Comment (Deriva- References tive) HCl: F: 285grad, <α>(D)20: 20 +2grad (1percent H2O)

Patent; Roussel-Uclaf; FRM3638; (1964); Chem.Abstr.; vol. 70; nb. 106375m; (1969), View in Reaxys

Association (MCS) (1) 1 of 1

Description (Association Association with compound (MCS))

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

6/16

2016-03-15 08:50:35

Solvent (Association (MCS))

tetradeuteriomethanol

Comment (Association (MCS))

ambient temperature

Partner (Association (MCS))

(+)-(2R,3R,11R,12R)-1,4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid

Lovely, Ann E.; Wenzel, Thomas J.; Tetrahedron Asymmetry; vol. 17; nb. 18; (2006); p. 2642 - 2648, View in Reaxys

Reaxys ID 7665920 View in Reaxys

4/14 Chemical Name: (S)-2-(diphenylmethyl)pyrrolidine hydrochloride Linear Structure Formula: C17H19N*ClH Molecular Formula: C17H19N*ClH Molecular Weight: 273.806 Type of Substance: heterocyclic InChI Key: KTGRJTGIWVDSKZ-NTISSMGPSA-N Note:

NH Cl

H

Substance Label (1) Label References 1*HCl

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

281 - 282

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys Density (1) 1 of 1

Density [g·cm-3]

1.17

Type (Density)

crystallographic

Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb. 1; (1997); p. 149 - 153, View in Reaxys Crystal Phase (1) Description (Crys- Comment (Crystal References tal Phase) Phase) Crystal structure determination

a=8.18 Angstroem, b=11.77 Angstroem, c=16.09 Angstroem, n=4.; Method of determination: Single Crystal X-ray Diffraction

Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb.

1; (1997); p. 149 - 153, View in Reaxys

Crystal System (1) Crystal System References rhombic

Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb. 1; (1997); p. 149 153, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.15 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

7/16

2016-03-15 08:50:35

Optical Rotatory Power [deg]

1.8

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

20

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys Space Group (1) Space Group 19

References Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb. 1; (1997); p. 149 153, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

400

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

400

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

100

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

solid

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

8/16

2016-03-15 08:50:35

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; chemical ionization (CI)

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys

Reaxys ID 23196367 View in Reaxys

5/14 CAS Registry Number: 23627-61-4 Chemical Name: (R)-2-(diphenylmethyl)pyrrolidine hydrochloride Linear Structure Formula: C17H19N*ClH Molecular Formula: C17H19N*ClH Molecular Weight: 273.806 InChI Key: KTGRJTGIWVDSKZ-PKLMIRHRSA-N Note:

NH HCl

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; Daiichi Sankyo Company, Limited; NAKAMURA, Yoshitaka; KITAWAKI, Takafumi; KANEDA, Takeshi; US2014/296569; (2014); (A1) English, View in Reaxys

Reaxys ID 8951094 View in Reaxys

6/14 N(2+)

C+

Linear Structure Formula: C17H19 Molecular Formula: C17H18N*H Molecular Weight: 237.345 Type of Substance: heterocyclic InChI Key: CFJNRHHTVSUPHP-INIZCTEOSA-O Note:

NH H+

Substance Label (1) Label References 28

Klumpp; Aguirre; Sanchez Jr.; de Leon; Organic letters; vol. 3; nb. 17; (2001); p. 2781 - 2784, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- ClSO2F; fluorosulfonic acid scopy) Temperature (NMR Spectroscopy) [°C]

-80

Comment (NMR Spectroscopy)

in the presence of inorganic compounds

Klumpp; Aguirre; Sanchez Jr.; de Leon; Organic letters; vol. 3; nb. 17; (2001); p. 2781 - 2784, View in Reaxys 2 of 2

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

9/16

2016-03-15 08:50:35

Solvents (NMR Spectro- acetone-d6 scopy) Klumpp; Aguirre; Sanchez Jr.; de Leon; Organic letters; vol. 3; nb. 17; (2001); p. 2781 - 2784, View in Reaxys

Reaxys ID 9027605 View in Reaxys

7/14 Linear Structure Formula: C17H20N(1+)*C13H11O3 (1-) Molecular Formula: C13H12O3*C17H19N Molecular Weight: 453.581 Type of Substance: heterocyclic InChI Key: CAGRJVXCVNVKNE-NTISSMGPSA-N Note:

O NH

O

OH

Substance Label (1) Label References 3

Cheung; Kang; Netherton; Scheffer; Trotter; Journal of the American Chemical Society; vol. 122; nb. 47; (2000); p. 11753 - 11754, View in Reaxys

Crystal Phase (1) Description (Crys- References tal Phase) Crystal structure determination

Cheung; Kang; Netherton; Scheffer; Trotter; Journal of the American Chemical Society; vol. 122; nb. 47; (2000); p. 11753 - 11754, View in Reaxys

Crystal System (1) Crystal System References monoclinic

Cheung; Kang; Netherton; Scheffer; Trotter; Journal of the American Chemical Society; vol. 122; nb. 47; (2000); p. 11753 - 11754, View in Reaxys

Space Group (1) Space Group 4

References Cheung; Kang; Netherton; Scheffer; Trotter; Journal of the American Chemical Society; vol. 122; nb. 47; (2000); p. 11753 - 11754, View in Reaxys

Reaxys ID 9442980 View in Reaxys

8/14 Chemical Name: (S)-2-(diphenylmethyl)pyrrolidine perchlorate Linear Structure Formula: C17H19N*ClHO4 Molecular Formula: C17H19N*ClHO4 Molecular Weight: 337.803 Type of Substance: heterocyclic InChI Key: ALJZDSOWRUSQON-NTISSMGPSA-N Note:

OH

N H O

Cl OO

Substance Label (1) Label References 1*HClO4

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

198 - 199

Solvent (Melting Point)

CH2Cl2; petroleum ether

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

10/16

2016-03-15 08:50:35

Concentration (Optical Rotatory Power)

0.51 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-1.9

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

20

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

400

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

400

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

100

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

solid

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

11/16

2016-03-15 08:50:35

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys

Reaxys ID 9444804 View in Reaxys

9/14

OH

N H

2

Chemical Name: (S)-2-(diphenylmethyl)pyrrolidine sulfate Linear Structure Formula: 2C17H19N*H2O4S Molecular Formula: 2C17H19N*H2O4S Molecular Weight: 572.769 Type of Substance: heterocyclic InChI Key: ORGRECXFQSMOPA-NTISSMGPSA-N Note:

HO

S OO

Substance Label (1) Label References 1*0.5H2SO4

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

239 - 242

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.53 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-9.6

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

20

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

400

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

12/16

2016-03-15 08:50:35

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

400

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

100

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

solid

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; fast atom bombardment (FAB)

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys

Reaxys ID 9444887 View in Reaxys

10/14 Chemical Name: (S)-2-(diphenylmethyl)pyrrolidine hydrogen sulfate Linear Structure Formula: C17H19N*H2O4S Molecular Formula: C17H19N*H2O4S Molecular Weight: 335.424 Type of Substance: heterocyclic InChI Key: ORGRECXFQSMOPA-NTISSMGPSA-N Note:

OH

N H HO

S OO

Substance Label (1) Label References 1*H2SO4

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

197 - 199

Solvent (Melting Point)

methanol; diethyl ether

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

13/16

2016-03-15 08:50:35

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.58 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-2.6

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

20

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

400

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

400

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

25

Frequency (NMR Spectroscopy) [MHz]

100

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys IR Spectroscopy (1)

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

14/16

2016-03-15 08:50:35

1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

solid

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) chemical ionization (CI)

Aggarwal, Varinder K.; Lopin, Chrystel; Sandrinelli, Franck; Journal of the American Chemical Society; vol. 125; nb. 25; (2003); p. 7596 - 7601, View in Reaxys

Reaxys ID 10629877 View in Reaxys

11/14 -1

Linear Structure Formula: C17H19N*BF4 (1-)*H(1+) Molecular Formula: BF4*C17H19N*H Molecular Weight: 325.157 Type of Substance: heterocyclic InChI Key: PNUFSMDYQFRPGP-NTISSMGPSA-O Note:

F (v4)

F

B FF

HN

H+

Substance Label (1) Label References 4

Biaggi, Cinzia; Benaglia, Maurizio; Raimondi, Laura; Cozzi, Franco; Tetrahedron; vol. 62; nb. 52; (2006); p. 12375 - 12379, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Biaggi, Cinzia; Benaglia, Maurizio; Raimondi, Laura; Cozzi, Franco; Tetrahedron; vol. 62; nb. 52; (2006); p. 12375 - 12379, View in Reaxys

Reaxys ID 10733495 View in Reaxys

NH

12/14

F F

Linear Structure Formula: C17H19N*CHF3O3S Molecular Formula: CHF3O3S*C17H19N Molecular Weight: 387.423 Type of Substance: heterocyclic InChI Key: ICBXTOBINPSWGM-NTISSMGPSA-N Note:

F O

S

OH O

Substance Label (1) Label References 1d

Chow, San San; Nevalainen, Marta; Evans, Catherine A.; Johannes, Charles W.; Tetrahedron Letters; vol. 48; nb. 2; (2007); p. 277 - 280, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

15/16

2016-03-15 08:50:35

Reaxys ID 14457637 View in Reaxys

13/14 CAS Registry Number: 702711-81-7 Linear Structure Formula: C2HF3O2*C17H19N Molecular Formula: C2HF3O2*C17H19N Molecular Weight: 351.369 InChI Key: LUWIZWOTKTZZEY-NTISSMGPSA-N Note:

O

NH

F

HO

F F

Substance Label (1) Label References IVd

Patent; JAPAN SCIENCE AND TECHNOLOGY AGENCY; WO2005/90294; (2005); (A2) English, View in Reaxys

Reaxys ID 18786546 View in Reaxys

NH

14/14 Linear Structure Formula: C17H19N*C50H57O4P Molecular Formula: C17H19N*C50H57O4P Molecular Weight: 990.318 InChI Key: NOUCZZVJSQZKKW-SFVHDIHTSA-N Note: O O P O

OH

R(a)-isomer

Substance Label (1) Label References 11bi

Patent; STUDIENGESELLSCHAFT KOHLE MBH; US2009/30216; (2009); (A1) English, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

16/16

2016-03-15 08:50:35