Hydrogen Bromide → HCID 46937585, compound

Participants

Reaction Steps

(2S,4S)-Methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-phenylpiperidine-1-carboxylate (249 mg, 0.82 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 3 mL, 42.82 mmol) and the mixture was stirred at room temperature for 16 h. The solvent was evaporated 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-((2S,4S)-2-phenylpiperidin-4-yl)isoxazol-3(2H)-one (255 mg, 127%) (the isolated sample contained DMSO). 1H NMR (400 MHz, cdcl3) δ 2.10-2.43 (m, 4H), 3.21 (dt, 1H), 3.26-3.35 (m, 1H), 3.35-3.43 (m, 1H), 4.17 (dd, 1H), 5.73 (s, 1H), 7.34-7.48 (m, 5H). HRMS Calculated for [C14H16N2O2+H]+: 245.1290. Found: 245.1271.

Provenance & Evidence