Hydrogen Bromide → HCID 66732396, compound

Participants

Reaction Steps

(2R,4R)-Methyl 2-(2,4-dichlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (75 mg, 0.20 mmol) (from example 51, step 3) was diluted with hydrogen bromide (33% in AcOH, 1062 μl, 6.06 mmol) and stirred at ambient temperature for 24 h. 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,4R)-2-(2,4-dichlorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (38 mg, 60%). 1H NMR (600 MHz, dmso) δ 1.47-1.54 (m, 1H), 1.78-1.85 (m, 1H), 1.93-1.99 (m, 1H), 2.05-2.11 (m, 1H), 2.67 (dt, 1H), 2.86-2.92 (m, 1H), 3.18-3.22 (m, 1H), 3.98 (dd, 1H), 5.93 (d, 1H), 7.41 (dd, 1H), 7.53 (d, 1H), 7.66 (d, 1H). HRMS Calculated for [C14H14Cl2N2O2+H]+: 313.0511. Found: 313.0494

Provenance & Evidence