Hydrogen Bromide → HCID 66732573, compound

Participants

Reaction Steps

Trans-methyl 2-(4-chlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (155 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-(trans-2-(4-chlorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (23.5 mg, 18%). 1H NMR (600 MHz, dmso) δ 1.74-1.83 (m, 2H), 1.84-1.91 (m, 1H), 1.96-2.03 (m, 1H), 2.70 (dt, 1H), 2.79-2.86 (m, 1H), 3.09-3.15 (m, 1H), 3.69 (dd, 1H), 5.89-5.98 (m, 1H), 7.32-7.36 (m, 2H), 7.36-7.41 (m, 2H). HRMS Calculated for [C14H15ClN2O2+H]+: 279.0900. Found: 279.0889

Provenance & Evidence