HCID 66735004, compound → HCID 46937587, compound

Participants

Reaction Steps

(2S,4S)-Methyl 2-cyclohexyl-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (79 mg, 0.26 mmol) was stirred in HBr (33% in AcOH) overnight. Evaporation of solvents and the residue purified by preparative HPLC (Instrument: FractionLynx I, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm.) to yield 5-((2S,4S)-2-cyclohexylpiperidin-4-yl)isoxazol-3(2H)-one 22 mg (35%). 1H NMR (400 MHz, cd3od) δ 1.00-1.39 (m, 5H), 1.51-1.64 (m, 1H), 1.64-1.93 (m, 6H), 1.96-2.11 (m, 1H), 2.15-2.25 (m, 1H), 2.26-2.35 (m, 1H), 2.92-3.02 (m, 1H), 3.03-3.16 (m, 1H), 3.22-3.33 (m, 2H), 5.57 (s, 1H). HRMS Calcd for [C14H22N2O2+H]+: 251.1760. Found: 251.1754.

Provenance & Evidence