HCID 66732072, compound → HCID 66732117, compound

Participants

Reaction Steps

Methyl 2-(4-chlorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (347 mg, 0.99 mmol) was stirred in HBr (33% in AcOH) overnight (19 hours). Evaporation of solvents 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) yielded 5-(trans-2-(4-chlorobenzyl)piperidin-4-yl)isoxazol-3(2H)-one (151 mg, 52%). 1H NMR (400 MHz, tfa) δ 2.25-2.60 (m, 4H), 3.06-3.20 (m, 2H), 3.35-3.52 (m, 1H), 3.55-3.75 (s, 2H), 3.77-3.96 (m, 1H), 6.59 (s, 1H), 7.15-7.22 (m, 2H), 7.22-7.41 (m, 2H). HRMS Calcd for [C15H17ClN2O2+H]+: 293.1057. Found: 293.1031.

Provenance & Evidence