Hydrogen Bromide → 5-(trans-2-(4-(Trifluoromethyl)phenyl)piperidin-4-yl)isoxazol-3(2h)-one

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Reaction Steps

Trans-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethyl)phenyl)piperidine-1-carboxylate (148 mg, 0.40 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 3 mL, 17.13 mmol) and the solution 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-(trifluoromethyl)phenyl)piperidin-4-yl)isoxazol-3(2H)-one (50 mg, 40%). 1H NMR (600 MHz, dmso) δ 1.75-1.83 (m, 2H), 1.84-1.92 (m, 1H), 2.00-2.06 (m, 1H), 2.70 (dt, 1H), 2.79-2.86 (m, 1H), 3.09-3.15 (m, 1H), 3.77 (d, 1H), 5.95 (s, 1H), 7.59 (d, 2H), 7.64 (d, 2H). HRMS Calculated for [C15H15F3N2O2+H]+: 313.1164. Found: 313.1166

Provenance & Evidence