Acetic Acid → HCID 66732547, compound

Participants

Reaction Steps

Trans-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(2-(trifluoromethyl)benzyl)piperidine-1-carboxylate (157 mg, 0.41 mmol) was dissolved in hydrogen bromide (33% in acetic acid (3 mL, 17.13 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-(trans-2-(2-(trifluoromethyl)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (53 mg, 40%). 1H NMR (600 MHz, cd3od) δ 1.95 (ddd, 1H), 2.08-2.19 (m, 2H), 2.19-2.28 (m, 1H), 3.07-3.18 (m, 2H), 3.18-3.25 (m, 1H), 3.33-3.43 (m, 2H), 3.51-3.62 (m, 1H), 5.75 (d, 1H), 7.43-7.51 (m, 2H), 7.63 (t, 1H), 7.73 (d, 1H). HRMS Calculated for [C16H17F3N2O2+H]+: 327.1320. Found: 327.1297

Provenance & Evidence