Sodium borohydride → (2-((Tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethyl)-phenyl)-(cyclopentyl)methanol

HRID 2075032Notes

Reaction equation

HRID 2075032 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=1[C:20]([CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:13]=[CH:12][C:11]=1[CH:20]([CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1)[OH:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67091601(2-((Tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethyl)-phenyl)-(cyclopentyl)-methanone

Product 1

HCID 58968632(2-((Tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethyl)-phenyl)-(cyclopentyl)methanolYield 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2-((tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethyl)-phenyl)-(cyclopentyl)-methanone (138 mg, 0.35 mmol) in methanol (0.5 mL) at room temperature was added sodium borohydride (40.5 mg, 1.07 mmol). The mixture was stirred at room temperature overnight. Methanol was removed in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to yield the title compound (126.8 mg, 91%). 1H NMR (400 MHz, CDCl3) δ ppm 0.13 (s, 3H) 0.14 (s, 3H) 0.94 (s, 9H) 1.04-1.12 (m, 1H) 1.43-1.74 (m, 6H) 1.87-1.97 (m, 1H) 2.30-2.44 (m, 1H) 2.62-2.75 (m, J=1.66 Hz, 1H) 4.64 (d, J=8.71 Hz, 1H) 4.77 (d, J=12.86 Hz, 1H) 4.92 (d, J=12.86 Hz, 1H) 7.55 (s, 2H) 7.66 (s, 1H).

Workup

  1. customMethanol was removed in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6ba0983e94d458f80ad739f00a4937a
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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