Hydrogen Bromide → HCID 46937482, compound

Participants

Reaction Steps

(2R,4S)-Methyl 2-(4-chloro-3,5-difluorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.39 g, 1.05 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 10 mL, 142.75 mmol) and stirred at room temperature for 18 h. 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-((2R,4S)-2-(4-chloro-3,5-difluorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (272 mg, 83%). 1H NMR (600 MHz, dmso) δ 1.29 (q, 1H), 1.43 (dq, 1H), 1.82-1.89 (m, 1H), 1.97-2.04 (m, 1H), 2.70 (dt, 1H), 2.84 (tt, 1H), 3.06-3.12 (m, 1H), 3.68 (dd, 1H), 5.73 (s, 1H), 7.31 (d, 2H). HRMS Calculated for [C14H13ClF2N2O2+H]+: 315.0712. Found: 315.0707

Provenance & Evidence