Hydrogen Bromide → HCID 66732362, compound

Participants

Reaction Steps

Trans-methyl 2-(4-chloro-3-fluorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (49 mg, 0.14 mmol) was dissolved in hydrogen bromide (33% in AcOH, 2 mL, 11.42 mmol) and stirred at room temperature for 5 h. The reaction was heated to 50° C. for 3 h. The reaction mixture was evaporated in vacuo 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-(trans-2-(4-chloro-3-fluorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (23 mg, 56%). 1H NMR (600 MHz, dmso) δ 1.72-1.81 (m, 2H), 1.82-1.89 (m, 1H), 1.97-2.04 (m, 1H), 2.64-2.71 (m, 1H), 2.77-2.83 (m, 1H), 3.06-3.12 (m, 1H), 3.72 (dd, 1H), 5.96 (s, 1H), 7.23 (dd, 1H), 7.40 (dd, 1H), 7.49 (t, 1H). HRMS Calculated for [C14H14ClFN2O2+H]+: 297.0806. Found: 297.0807

Provenance & Evidence