Hydrogen Bromide → HCID 66732863, compound

Participants

Reaction Steps

Trans-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(4-(trifluoromethoxy)benzyl)piperidine-1-carboxylate (0.603 g, 1.51 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 11.87 mL, 67.78 mmol) and the mixture was stirred at room temperature overnight. The solvent was evaporated and the compound was purified by preparative HPLC on a XBridge C18 column (10 μm 250×50 ID mm) using a gradient of 10-50% Acetonitrile in H2O/AcN/NH3 95/5/0.2 buffer over 20 minutes with a flow of 100 mL/min. 5-(Trans-2-(4-(trifluoromethoxy)benzyl)piperidin-4-yl)isoxazol-3(2H)-one (200 mg, 38.8%) was isolated as a white solid. 1H NMR (400 MHz, dmso) δ 1.47-1.60 (m, 1H), 1.68-1.87 (m, 3H), 2.43-4.01 (m, 6H), 5.73 (s, 1H), 7.20-7.40 (m, 4H). HRMS Calculated for [C16H17F3N2O3+H]+: 343.1270. Found: 343.1260

Provenance & Evidence