Acetic Acid → HCID 46937477, compound

Participants

Reaction Steps

(2R,4S)-Methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3,4,5-trifluorophenyl)piperidine-1-carboxylate (164 mg, 0.46 mmol) was dissolved in hydrogen bromide (33% in acetic acid (3.63 mL, 20.71 mmol) and the mixture was stirred at room temperature 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-((2R,4S)-2-(3,4,5-trifluorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (93 mg, 67%). 1H NMR (600 MHz, dmso) δ 1.29 (q, 1H), 1.43 (dq, 1H), 1.82-1.89 (m, 1H), 1.96-2.02 (m, 1H), 2.70 (dt, 1H), 2.79-2.87 (m, 1H), 3.05-3.12 (m, 1H), 3.64 (dd, 1H), 5.72 (s, 1H), 7.26-7.34 (m, 2H). HRMS Calculated for [C14H13F3N2O2+H]+: 299.1007. Found: 299.1002

Provenance & Evidence