Hydrogen Bromide → HCID 46938268, compound

Participants

Reaction Steps

(2R,4S)-Methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)-piperidine-1-carboxylate (74.5 mg, 0.20 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 1.58 mL, 9.03 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,4S)-2-(6-(trifluoromethyl)pyridin-3-yl)piperidin-4-yl)isoxazol-3(2H)-one (43 mg, 68%), 1H NMR (600 MHz, dmso) δ 1.36-1.53 (m, 2H), 1.89 (d, 1H), 2.04 (d, 1H), 2.70-2.78 (m, 1H), 2.90 (tt, 1H), 3.09-3.16 (m, 1H), 3.83 (d, 1H), 5.75 (s, 1H), 7.84 (d, 1H), 8.04 (dd, 1H), 8.75 (d, 1H). HRMS Calculated for [C14H14F3N3O2+H]+: 314.1116. Found: 314.1134

Provenance & Evidence