Hydrogen Bromide → HCID 46937582, compound

Participants

Reaction Steps

(2R,4S)-Methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (319 mg, 0.82 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 6.5 mL, 36.97 mmol) and stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was 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-((2R,4S)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-piperidin-4-yl)isoxazol-3(2H)-one (150 mg, 55%). 1H NMR (600 MHz, dmso) δ 1.33 (q, 1H), 1.45 (dq, 1H), 1.84-1.90 (m, 1H), 1.99-2.05 (m, 1H), 2.72 (dt, 1H), 2.83-2.91 (m, 1H), 3.07-3.14 (m, 1H), 3.72-3.79 (m, 1H), 5.73 (s, 1H), 7.41 (d, 1H), 7.48 (d, 1H), 7.70 (t, 1H). HRMS Calculated for [C15H14F4N2O2+H]+: 331.1070. Found: 331.1058.

Provenance & Evidence