Diethyl Ether → (1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(2-fluoro-3-(trifluoromethyl)phenyl)propan-1-ol

HRID 2279469Notes

Reaction equation

HRID 2279469 reaction equation
[Si:1]([O:8][C@@H:9]([CH3:23])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=1[F:22])=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCOCC>[BH4-].[Zn+2].[BH4-].O>[Si:1]([O:8][C@@H:9]([CH3:23])[C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:21])[F:20])[C:13]=1[F:22])[OH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 86705481(S)-2-(tert-butyldimethylsilyloxy)-1-(2-fluoro-3-(trifluoromethyl)phenyl)propan-1-one

Product 1

HCID 86705482(1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(2-fluoro-3-(trifluoromethyl)phenyl)propan-1-ol

Reagents, catalysts & solvents 2

HCID 12838295ZINC;boranuideCatalystHCID 962WaterSolvent

Procedure

To a solution of 112 (1.374 g, 3.921 mmol) and Et2O (20 mL) cooled to 0° C. was added a solution of zinc borohydride (8.46 mL, 1.176 mmol) was added and the reaction was stirred for 2 h. Water was added slowly and the mixture was extracted with ether. The organic layer was washed with water and brine then dried, filtered, and concentrated to afford (1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(2-fluoro-3-(trifluoromethyl)phenyl)propan-1-ol (114) which was used without additional purification.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ether
  3. washThe organic layer was washed with water and brine
  4. customthen dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-94ec11e52c684e60bb22c716627683e3
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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