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 221702Notes

Reaction equation

HRID 221702 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-4f78896b93a34be1be1b04d3cf1b145a
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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