Hydrogen Bromide → HCID 46937525, compound

Participants

Reaction Steps

(2S,4R)-Methyl 2-(3-methyl-4-(trifluoromethyl)phenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (0.168 g, 0.44 mmol) (from example 67, step 3) was dissolved in HBr (33% in acetic acid, 5.6 g, 22.84 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-((2S,4R)-2-(3-methyl-4-(trifluoromethyl)phenyl)piperidin-4-yl)isoxazol-3(2H)-one (0.068 g, 48%). 1H NMR (600 MHz, dmso) δ 1.31-1.40 (m, 1H), 1.41-1.50 (m, 1H), 1.85-1.90 (m, 1H), 1.95-2.00 (m, 1H), 2.40 (s, 3H), 2.69-2.76 (m, 1H), 2.83-2.90 (m, 1H), 3.08-3.13 (m, 1H), 3.68 (d, 1H), 5.73 (s, 1H), 7.36 (d, 1H), 7.43 (s, 1H), 7.57 (d, 1H). HRMS Calcd for [C16H17F3N2O2+H]+: 327.1320. Found: 327.1318.

Provenance & Evidence