Hydrogen Bromide → HCID 66732368, compound

Participants

Reaction Steps

(2S,4R)-Methyl 2-(2,5-difluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (499 mg, 1.42 mmol) (from example 124, step 3) was dissolved in hydrogen bromide (33% in acetic acid, 10 mL, 57.10 mmol) and the mixture stirred at room temperature for 22 h. The solvent was evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx III, 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-(2,5-difluorobenzyl)piperidin-4-yl)isoxazol-3(2H)-one (292 mg, 70%). 1H NMR (600 MHz, cd3od) δ 1.49 (q, 1H), 1.71 (dq, 1H), 2.00-2.08 (m, 2H), 2.83-2.91 (m, 2H), 2.93-3.00 (m, 2H), 3.25-3.31 (m, 1H), 3.33-3.37 (m, 1H), 5.50 (s, 1H), 6.99-7.12 (m, 3H). HRMS Calculated for [C15H16F2N2O2+H]+: 295.1258. Found: 295.1254

Provenance & Evidence