Hydrogen Bromide → HCID 46938213, compound

Participants

Reaction Steps

(2S,4R)-Methyl 4-(3-oxo-2,3-dihydroisoxazol-5-yl)-2-(3-(trifluoromethyl)phenyl)piperidine-1-carboxylate (0.152 g, 0.42 mmol) (from example 30, step 3) was dissolved in hydrogen bromide (33% in acetic acid, 3.30 mL, 18.83 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-(trifluoromethyl)phenyl)piperidin-4-yl)isoxazol-3(2H)-one (28 mg, 22%). 1H NMR (600 MHz, dmso) δ 1.35 (q, 1H), 1.47 (qd, 1H), 1.87 (d, 1H), 2.00 (d, 1H), 2.73 (dt, 1H), 2.84-2.91 (m, 1H), 3.09-3.14 (m, 1H), 3.75 (d, 1H), 5.74 (s, 1H), 7.50-7.54 (m, 1H), 7.55-7.58 (m, 1H), 7.66 (d, 1H), 7.71 (s, 1H). HRMS Calculated for [C15H15F3N2O2+H]+: 313.1164. Found: 313.1158

Provenance & Evidence