Hydrogen Bromide → HCID 46938321, compound

Participants

Reaction Steps

(2R,4S)-Methyl 2-(4-chloro-3-fluorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (446 mg, 1.26 mmol) was dissolved in hydrogen bromide (33% in AcOH, 6.8 mL, 38.97 mmol) and stirred at room temperature for 20 h. The solvent was then 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-((2R,4S)-2-(4-chloro-3-fluorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (266 mg, 71%). 1H NMR (600 MHz, dmso) δ 1.31 (q, 1H), 1.44 (dq, 1H), 1.82-1.89 (m, 1H), 1.94-2.00 (m, 1H), 2.70 (dt, 1H), 2.84 (tt, 1H), 3.06-3.12 (m, 1H), 3.66 (dd, 1H), 5.72 (s, 1H), 7.23 (dd, 1H), 7.38 (dd, 1H), 7.49 (t, 1H). HRMS Calculated for [C14H14ClFN2O2+H]+: 297.0806. Found: 297.0795

Provenance & Evidence