Acetic Acid → 5-(trans-2-(Cyclohexyloxymethyl)piperidin-4-yl)isoxazol-3(2h)-one

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Reaction Steps

Trans-methyl 2-(cyclohexyloxymethyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (121 mg, 0.36 mmol) was dissolved in hydrogen bromide (33% in acetic acid, (2.75 mL, 15.69 mmol) and stirred at room temperature for 16 h. The solvent was removed in vacuo 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-(cyclohexyloxymethyl)piperidin-4-yl)isoxazol-3(2H)-one (15 mg, 15%). 1H NMR (600 MHz, dmso) δ 1.09-1.25 (m, 5H), 1.38-1.53 (m, 2H), 1.55-1.65 (m, 2H), 1.65-1.83 (m, 5H), 2.55-2.63 (m, 1H), 2.69-2.80 (m, 2H), 3.02-3.88 (m, 4H), 5.76 (s, 1H). HRMS Calculated for [C15H24N2O3+H]+: 281.1865. Found: 281.1879

Provenance & Evidence