Hydrogen Bromide → HCID 46938266, compound

Participants

Reaction Steps

(2R,4S)-Methyl 2-(4-(methylsulfonyl)phenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (536 mg, 1.41 mmol) was dissolved in hydrogen bromide (33% in AcOH, 5 mL, 71.37 mmol) and stirred at room temperature for 20 h. The reaction mixture was evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx III, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-((2R,4S)-2-(4-(methylsulfonyl)phenyl)piperidin-4-yl)isoxazol-3(2H)-one (309 mg, 68%), 1H NMR (600 MHz, dmso) δ 1.39 (q, 1H), 1.49 (dq, 1H), 1.87-1.93 (m, 1H), 2.01 (d, 1H), 2.76 (t, 1H), 2.87-2.94 (m, 1H), 3.11-3.19 (m, 1H), 3.17 (s, 3H), 3.80 (d, 1H), 5.74 (s, 1H), 7.64 (d, 2H), 7.85 (d, 2H). HRMS Calcd for [C15H18N2O4S+H]+: 323.1065. Found: 323.1042.

Provenance & Evidence