Sodium borohydride → (2-((Tert-butyldimethylsilyloxy)methyl)-4-(trifluoromethyl)-phenyl)-(cyclopentyl)methanol
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
Product 1
Reagents, catalysts & solvents 1
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).