Hydrogen Bromide → HCID 46937478, compound

Participants

Reaction Steps

(2S,4R)-methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3,4,5-trifluorophenyl)piperidine-1-carboxylate (160 mg, 0.45 mmol) (from example 60, step 3) was dissolved in hydrogen bromide (33% in acetic acid, 3.54 mL, 20.21 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-((2S,4R)-2-(3,4,5-trifluorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (85 mg, 63%) 1H NMR (600 MHz, dmso) δ 1.29 (q, 1H), 1.43 (qd, 1H), 1.83-1.88 (m, 1H), 1.97-2.02 (m, 1H), 2.70 (td, 1H), 2.80-2.87 (m, 1H), 3.06-3.12 (m, 1H), 3.64 (dd, 1H), 5.73 (s, 1H), 7.27-7.34 (m, 2H). HRMS Calculated for [C14H13F3N2O2+H]+: 299.1007. Found: 299.1037

Provenance & Evidence