Hydrogen Bromide → HCID 46938163, compound

Participants

Reaction Steps

(2R,4S)-Methyl 2-(4-fluorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.86 g, 2.68 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 15.52 mL, 88.60 mmol) and the solution stirred at room temperature overnight. The solvent was evaporated and the residue was purified by preparative HPLC (Instrument: Agilent, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) and on a XBridge C18 column (10 μm 250×19 ID mm) using a gradient of 0-30% Acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 20 minutes with a flow of 19 mL/min. 5-((2R,4S)-2-(4-Fluorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (167 mg, 23%) was isolated. 1H NMR (400 MHz, dmso) δ 1.27-1.53 (m, 2H), 1.81-1.98 (m, 2H), 2.67-2.77 (m, 1H), 2.78-2.91 (m, 1H), 3.10 (d, 1H), 3.63 (d, 1H), 5.67-5.77 (m, 1H), 7.04-7.16 (m, 2H), 7.34-7.45 (m, 2H). HRMS Calculated for [C14H15FN2O2+H]+: 263.1196. Found: 263.1201

Provenance & Evidence