Hydrogen Bromide → HCID 66732069, compound

Participants

Reaction Steps

(2S,4R)-Methyl 2-(2,4-dichlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (340 mg, 0.92 mmol) (from example 51, step 3) was diluted with hydrogen bromide (33% in AcOH, 4812 μl, 27.48 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-((2S,4R)-2-(2,4-dichlorophenyl)piperidin-4-yl)isoxazol-3(2H)-one ( ). 1H NMR (600 MHz, dmso) δ 1.22 (q, 1H), 1.47 (dq, 1H), 1.84-1.90 (m, 1H), 1.96-2.03 (m, 1H), 2.74 (dt, 1H), 2.87 (tt, 1H), 3.07-3.15 (m, 1H), 3.96 (dd, 1H), 5.73 (s, 1H), 7.40 (dd, 1H), 7.54 (d, 1H), 7.64 (d, 1H). HRMS Calculated for [C14H14Cl2N2O2+H]+: 313.0511. Found: 313.0490

Provenance & Evidence