Hydrogen Bromide → HCID 46937643, compound

Participants

Reaction Steps

(2S,4S)-Methyl 2-((4,4-difluorocyclohexyl)methyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (0.787 g, 2.20 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 17.31 mL, 98.82 mmol) and the mixture 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,4S)-2-((4,4-difluorocyclohexyl)methyl)-piperidin-4-yl)isoxazol-3(2H)-one (424 mg, 64%). 1H NMR (600 MHz, DMSO) δ 0.98-1.41 (m, 5H), 1.51-2.61 (m, 12H), 2.66-2.75 (m, 1H), 2.95-3.04 (m, 1H), 5.59-5.67 (m, 1H). HRMS Calculated for [C15H22F2N2O2+H]+: 301.1728. Found: 301.1713

Provenance & Evidence