Hydrogen Bromide → HCID 46937584, compound

Participants

Reaction Steps

(2R,4S)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-phenylpiperidine-1-carboxylate (621 mg, 2.05 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 7 mL, 99.92 mmol) and the mixture stirred at room temperature for 24 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-((2R,4S)-2-phenylpiperidin-4-yl)isoxazol-3(2H)-one (306 mg, 61%) (the isolated sample contained DMSO). 1H NMR (400 MHz, cd3od) δ 1.76-2.02 (m, 2H), 2.11-2.30 (m, 2H), 3.05-3.21 (m, 2H), 3.41-3.49 (m, 1H), 4.14 (dd, 1H), 5.56 (s, 1H), 7.27-7.48 (m, 5H). HRMS Calculated for [C14H16N2O2+H]+: 245.1290. Found: 245.1270

Provenance & Evidence