Hydrogen Bromide → HCID 66731828, compound

Participants

Reaction Steps

(2R,4S)-Methyl 2-(2,4-dichlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (334 mg, 0.90 mmol) was diluted with hydrogen bromide (33% in AcOH, 4.7 mL, 26.99 mmol) and stirred at ambient temperature for 24 h. 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-(2,4-dichlorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (173 mg, 61%). 1H NMR (600 MHz, dmso) δ 1.22 (q, 1H), 1.47 (dq, 1H), 1.85-1.90 (m, 1H), 1.97-2.02 (m, 1H), 2.74 (dt, 1H), 2.87 (tt, 1H), 3.09-3.14 (m, 1H), 3.96 (dd, 1H), 5.73 (d, 1H), 7.40 (dd, 1H), 7.54 (d, 1H), 7.64 (d, 1H). HRMS Calculated for [C14H14Cl2N2O2+H]+: 313.0511. Found: 313.0493

Provenance & Evidence