Hydrogen Bromide → HCID 66732108, compound

Participants

Reaction Steps

Trans-methyl 2-(3-fluoro-5-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.255 g, 0.63 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 5 mL, 71.37 mmol) and stirred at room temperature for 1 week. The solvents were 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-(trans-2-(3-fluoro-5-(trifluoromethyl)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (172 mg, 79%). 1H NMR (600 MHz, dmso) δ 1.43-1.51 (m, 1H), 1.62-1.80 (m, 3H), 2.51-2.58 (m, 1H), 2.71-2.82 (m, 3H), 2.86-2.94 (m, 1H), 3.07-3.14 (m, 1H), 5.72 (s, 1H), 7.37-7.46 (m, 3H). HRMS Calculated for [C16H16F4N2O2+H]+: 345.1226. Found: 345.1241

Provenance & Evidence