Potassium Carbonate → Tert-butyl 4-hydroxy-4-(trifluoromethyl)piperidine-1-carboxylate

HRID 473811Notes

Reaction equation

HRID 473811 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]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68760848Tert-butyl 4-(trifluoromethyl)-4-(trimethylsilyloxy)piperidine-1-carboxylate

Product 1

HCID 22061329Tert-butyl 4-hydroxy-4-(trifluoromethyl)piperidine-1-carboxylateYield 17.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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+).

Workup

  1. filtrationFiltration and concentration
  2. customprovided an orange residue that
  3. customwas purified by silica gel chromatography (97:3 dichloromethane:methanol)

Sources & evidence

ORD record
ord-d1916dd9ce1e4ce7af64cfd499a85e6e
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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