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

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NH

1. Query

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Date

11 reactions in Reaxys

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

Search as: As drawn

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H O

N

HN

H

O

Rx-ID: 4636207 View in Reaxys 1/11 Yield

Conditions & References

86 %

With hydrogen, palladium on activated charcoal in methanol, Time= 48h, Ambient temperature Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb. 1; (1997); p. 149 - 153 View in Reaxys

76 %

With 10 palladium on charcoal, hydrogen in methanol, Time= 49h, T= 20 °C Kobayashi, Shoji; Kinoshita, Tatsuhiro; Uehara, Hisatoshi; Sudo, Tomoko; Ryu, Llhyong; Organic Letters; vol.

11; nb. 17; (2009); p. 3934 - 3937 View in Reaxys With hydrogen, palladium on activated charcoal Fernandez, Rosario; Martin-Zamora, Eloisa; Pareja, Carmen; Vazquez, Juan; Diez, Elena; Monge, Angeles; Lassaletta; Angewandte Chemie - International Edition; vol. 37; nb. 24; (1999); p. 3428 - 3430 View in Reaxys With hydrogen, palladium on activated charcoal, Hydrogenolysis Pareja, Carmen; Martin-Zamora, Eloisa; Fernandez, Rosario; Lassaletta, Jose M.; Journal of Organic Chemistry; vol. 64; nb. 24; (1999); p. 8846 - 8854 View in Reaxys

N

H

HN

H

Rx-ID: 3263508 View in Reaxys 2/11 Yield

Conditions & References

91 %

With hydrogen, palladium on activated charcoal in ethanol, Time= 3h, Heating 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

O

O O N

HN

H

O

Rx-ID: 17384589 View in Reaxys 3/11 Yield

Conditions & References Reaction Steps: 2 1: 82 percent / tetrahydrofuran / 3 h / Heating 2: 86 percent / H2 / Pd/C / methanol / 48 h / Ambient temperature With hydrogen, palladium on activated charcoal in tetrahydrofuran, methanol Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb. 1; (1997); p. 149 - 153 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.

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Br Mg

HN

H

Rx-ID: 17385274 View in Reaxys 4/11 Yield

Conditions & References Reaction Steps: 2 1: 82 percent / tetrahydrofuran / 3 h / Heating 2: 86 percent / H2 / Pd/C / methanol / 48 h / Ambient temperature With hydrogen, palladium on activated charcoal in tetrahydrofuran, methanol Bailey, David J.; O'Hagan, David; Tavasli, Mustafa; Tetrahedron Asymmetry; vol. 8; nb. 1; (1997); p. 149 - 153 View in Reaxys

O N

O H HN

H

Rx-ID: 19550716 View in Reaxys 5/11 Yield

Conditions & References Reaction Steps: 3 1: 75 percent / diethyl ether / 2 h / Heating 2: 72 percent / Li, NH3 / diethyl ether; tetrahydrofuran / 3 h / -45 °C 3: 91 percent / H2 / 10 percent Pd/C / ethanol / 3 h / Heating With ammonia, hydrogen, lithium, palladium on activated charcoal in tetrahydrofuran, diethyl ether, ethanol 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

HO N

HN

H

H

Rx-ID: 19553534 View in Reaxys 6/11 Yield

Conditions & References Reaction Steps: 2 1: 72 percent / Li, NH3 / diethyl ether; tetrahydrofuran / 3 h / -45 °C 2: 91 percent / H2 / 10 percent Pd/C / ethanol / 3 h / Heating With ammonia, hydrogen, lithium, palladium on activated charcoal in tetrahydrofuran, diethyl ether, ethanol 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

H N

O OH

HN

H

Rx-ID: 19566671 View in Reaxys 7/11

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.

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Yield

Conditions & References Reaction Steps: 5 1: thionylchloride / -30 deg C to Rt, reflux, 1 h 2: triethylamine / ethanol / 4 h / Heating 3: 75 percent / diethyl ether / 2 h / Heating 4: 72 percent / Li, NH3 / diethyl ether; tetrahydrofuran / 3 h / -45 °C 5: 91 percent / H2 / 10 percent Pd/C / ethanol / 3 h / Heating With thionyl chloride, ammonia, hydrogen, lithium, triethylamine, palladium on activated charcoal in tetrahydrofuran, diethyl ether, ethanol 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

O

H N

O

HN

H

Rx-ID: 19566708 View in Reaxys 8/11 Yield

Conditions & References Reaction Steps: 4 1: triethylamine / ethanol / 4 h / Heating 2: 75 percent / diethyl ether / 2 h / Heating 3: 72 percent / Li, NH3 / diethyl ether; tetrahydrofuran / 3 h / -45 °C 4: 91 percent / H2 / 10 percent Pd/C / ethanol / 3 h / Heating With ammonia, hydrogen, lithium, triethylamine, palladium on activated charcoal in tetrahydrofuran, diethyl ether, ethanol 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

O F

O S OH

N

F

F

F F

OH

F

S O

O

O

N H

O

Rx-ID: 10503982 View in Reaxys 9/11 Yield

Conditions & References in dichloromethane 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.

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O O

N H

P O

OH

R(a)-isomer

Rx-ID: 28261126 View in Reaxys 10/11 Yield 100 %

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

HN

Rx-ID: 6822553 View in Reaxys 11/11 Yield

Conditions & References Carbinol II, HI, Na2S2O3 Patent; Roussel-Uclaf; FRM3638; (1964); ; vol. 70; nb. 106375m; (1969) 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.

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