Acetic Acid → HCID 46938270, compound

Participants

Reaction Steps

(2R,4S)-methyl 2-(2-chloro-4-fluorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (382 mg, 1.08 mmol) was dissolved in hydrogen bromide (33% in acetic acid (8.5 mL, 48.46 mmol) and stirred at room temperature for 16 h. The solvent was removed in vacuo 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-(2-chloro-4-fluorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (304 mg, 95%). 1H NMR (600 MHz, dmso) δ 1.24 (q, 1H), 1.47 (dq, 1H), 1.85-1.91 (m, 1H), 1.97-2.02 (m, 1H), 2.75 (dt, 1H), 2.87 (tt, 1H), 3.09-3.14 (m, 1H), 3.97 (d, 1H), 5.73 (d, 1H), 7.19 (dt, 1H), 7.37 (dd, 1H), 7.66 (dd, 1H). HRMS Calculated for [C14H14ClFN2O2+H]+: 297.0806. Found: 297.0834

Provenance & Evidence