Hydrogen Bromide → HCID 66732671, compound

Participants

Reaction Steps

(2S,4S)-methyl 2-(4-chloro-2-fluorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.45 g, 1.27 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 10.00 mL, 57.08 mmol) and the mixture was stirred at room temperature overnight. The solvent was 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-(trans-2-(4-chloro-2-fluorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (82 mg, 22%). 1H NMR (400 MHz, dmso) δ 1.66-1.77 (m, 1H), 1.77-1.90 (m, 1H), 1.92-2.00 (m, 1H), 2.02-2.10 (m, 1H), 2.63-2.79 (m, 1H), 2.88-2.97 (m, 1H), 3.03-3.86 (omitted signals), 3.95 (d, 1H), 5.88 (s, 1H), 7.27 (dd, 1H), 7.35 (dd, 1H), 7.56 (t, 1H). HRMS Calcd for [C14H14ClFN2O2+H]+: 297.0806. Found: 297.0806.

Provenance & Evidence