sodium (trifluoroacetoxy)borohydride [NaBH3(OTFA), NaBH3(OCOCF3)] [InChIKey XXCYUERWFPDSIE-UH

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2 reactions in Reaxys

2016-03-23 08h:53m:01s (EST)

F O F

1. Query

Na +

F O

(v0)

– (v4)

H 3B

Search as: As drawn

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2016-03-23 08:56:39

F

F

F O

HO

F Na +

F

F

O

–H

O B

3

Rx-ID: 23569636 View in Reaxys 1/2 Yield

Conditions & References 27 :To a suspension of sodium borohydride (528 mg, 13.9 mmol) in tetrahydrofuran (10ml) was addedtrifluoroacetic acid (1.6 g, 13.9 mmol) dropwise at room temperature over 10 mins to give a solution of sodium trifluoroacetoxyborohydride[NaBH3 (OCOCF3)]. To this was added a solution of2-fluoro-4- (trifluoromethyl) phenylacetonitrile (2.83 g, 13.9 mmol) in tetrahydrofuran (5 ml) and the resulting solution stirred at RT for 20hrs. The reaction was quenched by the addition of water(1 ml) and then evaporated in vacuo and the resulting oil was dissolved in dichloromethane and loaded onto a <Desc/Clms Page number 48>strong cation exchange (SCX) cartridge. The cartridge was washed with dichloromethance and methanol then the product eluted with 2M ammonia in methanol. This gave the title compound as a brown oil (900 mg, 31percent).'H NMR (360 MHz; DMSO) 8 7.65-7.55 (3H, m), 5.89-5. 45 (2H, br s), 2.98-2. 88 (4H, m). M/z (ES+) 208 (M+H+).

With sodium tetrahydroborate in tetrahydrofuran, Time= 0.166667h, T= 20 °C Patent; MERCK SHARP and DOHME LIMITED; HOLLINGWORTH, Gregory, John; JONES, A., Brian; SPAREY, Timothy, Jason; WO2005/49613; (2005); (A1) English View in Reaxys

F BH–4

Na

+

F

F O

HO

F Na +

F O

F –H

O 3B

Rx-ID: 23656965 View in Reaxys 2/2 Yield

Conditions & References 11 :[0134] Preparation of Na(BH3(OCOCF3)). Trifluoroacetic acid (0.14 ml, 0.207 g, 1.82 mmol) was added dropwise with an airtight syringe to a suspension of sodium borohydride (0.072 g, 1.90 mmol) in TV (2 ml) cooled to 10-15° C. and maintained under an atmosphere of nitrogen. The mixture was stirred at room temperature for 10 minutes to give a clear solution. in 2,5-diphenyl-3-[α-naphthyl]-tetrazolium chloride, Time= 0.166667h, T= 10 - 20 °C , Product distribution / selectivity Patent; Khachik, Frederick; US2003/220525; (2003); (A1) English View in Reaxys 12 :[0136] Preparation of Na(BH3(OCOCF3)), Trifluoroacetic acid (0.14 ml, 0.207 g, 1.82 mmol) was added dropwise with an airtight syringe to a suspension of sodium borohydride (0.072 g, 1.90 mmol) in THE (2 ml) cooled to 10-l 5° C. and maintained under an atmosphere of nitrogen. The mixture was stirred at room temperature for 10 minutes to give a clear solution. in 3α,17α,21-trihydroxy-5α-pregnane-11,20-dione, Time= 0.166667h, T= 10 - 20 °C , Product distribution / selectivity Patent; Khachik, Frederick; US2003/220525; (2003); (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.

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2016-03-23 08:56:39