2-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-3,3,3-trifluoro-propionic acid ethyl ester → [1-(3-Bromo-phenyl)-2,2,2-trifluoro-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

HRID 81550Notes

Reaction equation

HRID 81550 reaction equation
C([O:3][C:4](=O)[C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[CH:19]=1)([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]([F:9])([F:8])[F:7])C>C1(C)C=CC=CC=1>[C:14]([O:13][C:11](=[O:12])[NH:10][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[CH:19]=1)([CH2:4][OH:3])[C:6]([F:7])([F:8])[F:9])([CH3:17])([CH3:15])[CH3:16]

Participants

3

Reactant 1

HCID 666657032-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-3,3,3-trifluoro-propionic acid ethyl ester

Product 1

HCID 66665702[1-(3-Bromo-phenyl)-2,2,2-trifluoro-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To an at −7° C. stirred solution of 5 g (11.73 mmol) 2-(3-bromo-phenyl)-2-tert-butoxycarbonylamino-3,3,3-trifluoro-propionic acid ethyl ester in 50 ml toluene were added 58.7 ml of a 1.7M solution of DibalH in toluene. The mixture was stirred overnight at rt and quenched with an aqueous tartaric acid solution. The mixture was extracted with EtOAc and the organic phase was washed with brine, dried with MgSO4.H2O and evaporated. Purification via chromatography on silica gel (c-hexane/15-50% TBME) gave the desired product as a colorless resin.

Workup

  1. customquenched with an aqueous tartaric acid solution
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic phase was washed with brine
  4. dry with materialdried with MgSO4.H2O
  5. customevaporated
  6. customPurification via chromatography on silica gel (c-hexane/15-50% TBME)

Sources & evidence

ORD record
ord-8cf5bebfe9504cf496a6d214a2cdc3f9
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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