HCID 68503455, compound → HCID 46937586, compound

Participants

Reaction Steps

(2R,4S)-Methyl 2-cyclohexyl-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.427 g, 1.38 mmol) was stirred in HBr (33% in AcOH) overnight (19 hours). Evaporation of solvents and the residue purified by preparative HPLC (Instrument: FractionLynx I, 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,4S)-2-cyclohexylpiperidin-4-yl)isoxazol-3(2H)-one (228 mg, 66%). 1H NMR (400 MHz, cd3od) δ 1.05-1.42 (m, 5H), 1.49-1.66 (m, 2H), 1.67-1.91 (m, 6H), 2.17-2.26 (m, 1H), 2.26-2.35 (m, 1H), 2.97-3.19 (m, 3H), 3.43-3.52 (m, 1H), 5.70 (s, 1H), 8.51 (s, 1H). HRMS Calcd for [C14H22N2O2+H]+: 251.1760. Found: 251.1750.

Provenance & Evidence