Hydrogen Bromide → HCID 66732268, compound

Participants

Reaction Steps

(2R,4S)-Methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(2-(trifluoromethyl)benzyl)piperidine-1-carboxylate (597 mg, 1.55 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 10 mL, 57.10 mmol) and the mixture stirred at room temperature overnight. The solvent was evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx III, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-((2R,4S)-2-(2-(trifluoromethyl)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (358 mg, 71%). 1H NMR (600 MHz, cd3od) δ 1.68 (q, 1H), 1.84 (qd, 1H), 2.11 (d, 1H), 2.22 (d, 1H), 3.02-3.20 (m, 3H), 3.21-3.32 (m, 1H), 3.51 (d, 1H), 3.57-3.67 (m, 1H), 5.74 (s, 1H), 7.44-7.56 (m, 2H), 7.64 (t, 1H), 7.74 (d, 1H). HRMS Calculated for [C16H17F3N2O2+H]+: 327.1320. Found: 327.1328

Provenance & Evidence