Hydrogen Bromide → HCID 46938323, compound

Participants

Reaction Steps

(2S,4R)-Methyl 2-(3,5-dichlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (1 g, 2.69 mmol) (from example 55, step 3) was dissolved in hydrogen bromide (33% in AcOH, 4.67 mL, 80.82 mmol) and stirred overnight. 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-(3,5-dichlorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (509 mg, 60%). 1H NMR (600 MHz, dmso) δ 1.32 (q, 1H), 1.44 (dq, 1H), 1.84-1.89 (m, 1H), 1.97-2.02 (m, 1H), 2.70 (dt, 1H), 2.84 (tt, 1H), 3.07-3.12 (m, 1H), 3.67 (dd, 1H), 5.75 (s, 1H), 7.42 (d, 2H), 7.44 (t, 1H). HRMS Calculated for [C14H14Cl2N2O2+H]+: 313.0511. Found: 313.0516

Provenance & Evidence