Hydrogen Bromide → HCID 66732462, compound

Participants

Reaction Steps

(2R,4S)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethoxy)benzyl)-piperidine-1-carboxylate (0.690 g, 1.72 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 13.58 mL, 77.56 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-(4-(trifluoromethoxy)benzyl)-piperidin-4-yl)isoxazol-3(2H)-one (55 mg, 9.4%). 1H NMR (600 MHz, dmso) δ 1.07 (q, 1H), 1.34 (dq, 1H), 1.69-1.78 (m, 2H), 2.45-2.74 (m, 5H), 2.93-2.99 (m, 1H), 5.64 (s, 1H), 7.20-7.25 (m, 2H), 7.26-7.32 (m, 2H). HRMS Calculated for [C16H17F3N2O3+H]+: 343.1270. Found: 343.1241

Provenance & Evidence