Acetic Acid → HCID 46937583, compound

Participants

Reaction Steps

(2S,4R)-Methyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (332 mg, 0.85 mmol) was dissolved in hydrogen bromide (33% in acetic acid (6.74 mL, 38.47 mmol) and stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was 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,4R)-2-(3-fluoro-4-(trifluoromethyl)phenyl)-piperidin-4-yl)isoxazol-3(2H)-one (174 mg, 62%). 1H NMR (600 MHz, dmso) δ 1.32 (q, 1H), 1.45 (dq, 1H), 1.85-1.90 (m, 1H), 2.00-2.04 (m, 1H), 2.72 (dt, 1H), 2.87 (tt, 1H), 3.08-3.13 (m, 1H), 3.73-3.77 (m, 1H), 5.73 (s, 1H), 7.41 (d, 1H), 7.48 (d, 1H), 7.70 (t, 1H). HRMS Calculated for [C15H14F4N2O2+H]+: 331.1070. Found: 331.1067.

Provenance & Evidence