Potassium Carbonate → Tert-butyl 4-hydroxy-4-(trifluoromethyl)piperidine-1-carboxylate
Reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1([O:16][Si](C)(C)C)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:16][C:3]1([C:2]([F:22])([F:1])[F:21])[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])[CH2:7][CH2:8]1Participants
4
Procedure
To a solution of tert-butyl 4-(trifluoromethyl)-4-(trimethylsilyloxy)piperidine-1-carboxylate (0.512 g, 1.50 mmol), in methanol (10 mL) was potassium carbonate (0.25 g, 1.81 mmol). The resulting mixture was stirred at room temperature for 12 hours. Filtration and concentration provided an orange residue that was purified by silica gel chromatography (97:3 dichloromethane:methanol) to give tert-butyl 4-hydroxy-4-(trifluoromethyl)piperidine-1-carboxylate (0.07 g, 14% yield). MS (EI) for C11H18F3NO3: 269 (MH+).