Hydrogen Bromide → HCID 66732779, compound

Participants

Reaction Steps

(2R,4R)-Methyl 2-(3,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.244 g, 0.69 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 5.46 mL, 31.16 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-((2R,4R)-2-(3,5-difluorobenzyl)piperidin-4-yl)isoxazol-3(2H)-one (51 mg, 25%). 1H NMR (600 MHz, dmso) δ 1.44-1.51 (m, 1H), 1.65-1.80 (m, 3H), 2.52-2.60 (m, 1H), 2.65-2.70 (m, 2H), 2.76-2.83 (m, 1H), 2.86-2.94 (m, 1H), 3.09-3.14 (m, 1H), 5.74 (s, 1H), 6.90-6.95 (m, 2H), 7.00 (tt, 1H). HRMS Calculated for [C15H16F2N2O2+H]+: 295.1258. Found: 295.1276

Provenance & Evidence