Water → (S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propan-1-ol

HRID 1452699Notes

Reaction equation

HRID 1452699 reaction equation
C([O:8][C:9](=O)[C@@H:10]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:21][C:20]=1[CH3:44])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C1C=CC=CC=1.[BH4-].[Na+].O>CO.C1COCC1>[CH3:44][C:20]1[CH:21]=[C:22]([C:25]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=2)([C:26]([F:27])([F:28])[F:29])[C:30]([F:32])([F:33])[F:31])[CH:23]=[CH:24][C:19]=1[O:18][C@@H:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][OH:8]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86604228(S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propionic acid benzyl ester

Product 1

HCID 86604230(S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propan-1-olYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.7 g (2.7 mmol) of (S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propionic acid benzyl ester was dissolved in a mixture of 11 mL of methanol and 11 mL of THF and cooled to 0° C. To this solution 1.0 g (26.9 mmol) of NaBH4 were added in portions, and the mixture was slowly warmed to room temperature overnight. Water was added, the phases were separated and the inorganic one was extracted with dichloromethane. The combined organic phases were washed with brine, dried (Na2SO4), filtered and evaporated. Purification by column chromatography with CH2Cl2/MeOH 95:5 yielded 960 mg (68%) (S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propan-1-ol as a light yellow oil, MS: 528 (M)+.

Workup

  1. temperaturethe mixture was slowly warmed to room temperature overnight
  2. customthe phases were separated
  3. extractionthe inorganic one was extracted with dichloromethane
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by column chromatography with CH2Cl2/MeOH 95:5

Sources & evidence

ORD record
ord-aaee2b92ed6249229a79e69c4e5e3a3b
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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