Ethyl Acetate → HCID 59444282, compound

Participants

Reaction Steps

To a solution of 2-(trimethylsilyl)ethyl(S)-2-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidine-1-carbonyl)-3-methylbutylcarbamate (110 mg, 0.221 mmol) in THF (1 mL) was added 1 equivalent of 1 M-tetra-N-butylammonium fluoride (0.221 mL, 0.221 mmol). The resulting mixture was stirred at room temperature for 1.5 hrs. After this time, the reaction was analyzed by LC/MS, which showed that the reaction was very slow. An additional 4 equiv. of TBAF (0.88 ml) was added and the mixture was stirred at room temperature for an additional 24 hour. After this time, the reaction mixture was added to EtOAc, washed with water and brine, dried over Na2SO4 and evaporated to give an oily residue. The oily residue was purified by Combiflash chromatography (24 g silica gel) with elution by 6:4 EtOAc-hexane to give the title compound (85.3 mg). MS (ESI+)=353.13 (M+H)+

Provenance & Evidence