Hydrogen Bromide → HCID 46937760, compound

Participants

Reaction Steps

Hydrogen bromide (33% in acetic acid, 5 mL) was added to a reaction flask containing (2S,4S)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)benzyl)piperidine-1-carboxylate (77 mg, 0.20 mmol). The reaction was stirred vigorously overnight. The solvent was evaporated. Purification using PrepLC (pH=11, small column, sample dissolved in MeOH, gradient 5-45, 20 min) yielded 5-((2S,4S)-2-(4-(trifluoromethyl)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (50 mg, 76%). 1H NMR (600 MHz, cd3od) δ 1.73-1.79 (m, 1H), 1.98-2.12 (m, 3H), 2.93 (dd, 1H), 2.97-3.04 (m, 2H), 3.17-3.25 (m, 2H), 3.35-3.41 (m, 1H), 5.48 (s, 1H), 7.41 (d, 2H), 7.61 (d, 2H). HRMS Calcd for [C16H17F3N2O2+H]+: 327.1320. Found: 327.1289.

Provenance & Evidence