Hydrogen Bromide → HCID 66732459, compound

Participants

Reaction Steps

Trans-methyl 2-(difluoromethyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (122 mg, 0.44 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 8.21 mL, 46.87 mmol) and stirred at room temperature for 16 h. The solvent was removed in vacuo and the compound was purified by preparative HPLC on a XBridge C18 column (10 μm 250×19 ID mm) using a gradient of 0-10% Acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 20 minutes with a flow of 19 mL/min. 5-(Trans-2-(difluoromethyl)piperidin-4-yl)isoxazol-3(2H)-one (86 mg, 89%) was isolated. 1H NMR (400 MHz, cd3od) δ 1.80-2.00 (m, 3H), 2.03-2.12 (m, 1H), 2.76-2.86 (m, 1H), 2.93-3.13 (m, 2H), 3.22-3.28 (m, 1H), 5.78 (s, 1H), 5.81 (dt, 1H). MS m/z 219 (M+H)+

Provenance & Evidence