Hydrogen Bromide → HCID 46938210, compound

Participants

Reaction Steps

(2S,4R)-Methyl 2-(4-chlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.458 g, 1.36 mmol) (from example 27, step 3) was dissolved in hydrogen bromide (33% in acetic acid, 10.72 mL, 61.20 mmol) and the mixture was stirred at room temperature overnight. The solvent was 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-((2S,4R)-2-(4-chloro-phenyl)piperidin-4-yl)isoxazol-3(2H)-one (198 mg, 52%). 1H NMR (600 MHz, dmso) δ 1.32 (q, 1H), 1.44 (dq, 1H), 1.83-1.88 (m, 1H), 1.91-1.96 (m, 1H), 2.71 (dt, 1H), 2.84 (tt, 1H), 3.07-3.11 (m, 1H), 3.63 (dd, 1H), 5.70 (s, 1H), 7.31-7.40 (m, 4H). HRMS Calculated for [C14H15ClN2O2+H]+: 279.0900. Found: 279.0887

Provenance & Evidence