Hydrogen Bromide → HCID 66732722, compound

Participants

Reaction Steps

(2S,4R)-Methyl 2-(3-fluoro-5-(trifluoromethyl)benzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.675 g, 1.68 mmol) (from example 137, step 3) was dissolved in hydrogen bromide (33% in AcOH, 5 mL, 71.37 mmol) and stirred at room temperature overnight. The solvents were evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-((2S,4R)-2-(3-fluoro-5-(trifluoromethyl)benzyl)-piperidin-4-yl)isoxazol-3(2H)-one (443 mg, 77%). 1H NMR (600 MHz, dmso) δ 1.08 (q, 1H), 1.31 (qd, 1H), 1.75 (t, 2H), 2.48-2.54 (m, 1H), 2.64-2.79 (m, 4H), 2.96 (d, 1H), 5.65 (s, 1H), 7.38-7.46 (m, 3H). HRMS Calculated for [C16H16F4N2O2+H]+: 345.1226. Found: 345.1212.

Provenance & Evidence