Hydrogen Bromide → HCID 46937761, compound

Participants

Reaction Steps

Hydrogen bromide (33% in acetic acid, 5 mL) was added to a reaction flask containing (2R,4R)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)benzyl)piperidine-1-carboxylate (87 mg, 0.23 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-((2R,4R)-2-(4-(trifluoromethyl)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (48 mg, 65%). 1H NMR (600 MHz, cd3od) δ 1.74-1.80 (m, 1H), 1.99-2.13 (m, 3H), 2.94 (dd, 1H), 2.98-3.05 (m, 2H), 3.19-3.26 (m, 2H), 3.36-3.42 (m, 1H), 5.50 (s, 1H), 7.42 (d, 2H), 7.62 (d, 2H). HRMS Calcd for [C16H17F3N2O2+H]+: 327.1320. Found: 327.1289.

Provenance & Evidence