Hydrogen Bromide → HCID 66732200, compound

Participants

Reaction Steps

(2S,4R)-Methyl 2-(4-(methylsulfonyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (225 mg, 0.57 mmol) was dissolved in HBr (33% in acetic acid, 5 mL, 28.55 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-(methylsulfonyl)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (91 mg, 47.4%). 1H NMR (600 MHz, dmso) δ 1.05-1.14 (m, 1H), 1.30-1.38 (m, 1H), 1.72-1.79 (m, 2H), 2.39-2.56 (omitted signals), 2.62-2.80 (m, 4H), 2.94-3.00 (m, 1H), 3.16 (s, 3H), 5.68 (s, 1H), 7.46 (d, 2H), 7.80 (d, 2H). HRMS Calcd for [C16H20N2O4S+H]+: 337.1222. Found: 337.1198

Provenance & Evidence