trans-Methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)benzyl)piperidine-1-carboxylate → 5-(trans-2-(3-(Trifluoromethyl)benzyl)piperidin-4-yl)isoxazol-3(2h)-one

Participants

Reaction Steps

Hydrogen bromide (33% in acetic acid, 10 mL) was added to a reaction flask containing trans-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)benzyl)piperidine-1-carboxylate (0.25 g, 0.65 mmol). The reaction was stirred vigorously overnight. The solvent was evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-(trans-2-(3-(trifluoromethyl)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (91 mg, 43%). 1H NMR (600 MHz, cd3od) δ 1.94-2.05 (m, 1H), 2.11-2.30 (m, 3H), 3.09-3.26 (m, 3H), 3.37-3.47 (m, 2H), 3.58-3.66 (m, 1H), 5.83 (s, 1H), 7.53-7.67 (m, 4H). HRMS Calculated for [C16H17F3N2O2+H]+: 327.1320. Found: 327.1322

Provenance & Evidence