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

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Reaction Steps

Trans-methyl 2-(3,5-difluoro-4-(trifluoromethyl)phenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (26 mg, 0.06 mmol) was dissolved in hydrogen bromide (33% in AcOH, 2 mL, 0.06 mmol) and stirred at room temperature for 20 h. 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-(3,5-difluoro-4-(trifluoromethyl)phenyl)piperidin-4-yl)isoxazol-3(2H)-one (7.00 mg, 31%). 1H NMR (600 MHz, dmso) δ 1.73-1.88 (m, 3H), 2.02-2.08 (m, 1H), 2.64-2.70 (m, 1H), 2.77-2.83 (m, 1H), 3.06-3.11 (m, 1H), 3.83-3.86 (m, 1H), 6.02 (s, 1H), 7.42 (d, 2H). HRMS Calcd for [C15H13F5N2O2+H]+: 349.0975. Found: 349.0983.

Provenance & Evidence