(2R,4S)-Methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate → 5-((2R,4S)-2-(3,3-Dimethylbutyl)piperidin-4-yl)isoxazol-3(2H)-one

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Reaction Steps

(2R,4S)-Methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (62 mg, 0.2 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 4 mL) and the mixture was stirred at room temperature for 18 h. The solvent was evaporated and the compound was purified by preparative HPLC on a XBridge C18 column (10 μm 250×19 ID mm) using a gradient of 5-30% Acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 15 minutes with a flow of 19 mL/min. 5-((2R,4S)-2-(3,3-Dimethylbutyl)piperidin-4-yl)isoxazol-3(2H)-one (39.8 mg, 79%) was isolated as a white solid. 1H NMR (600 MHz, cd3od) δ 0.92 (s, 9H), 1.20-1.34 (m, 2H), 1.56-1.69 (m, 2H), 1.83-1.90 (m, 1H), 2.05-2.13 (m, 1H), 2.14-2.21 (m, 1H), 2.26-2.34 (m, 1H), 3.05-3.19 (m, 2H), 3.25-3.34 (m, 2H), 5.75 (s, 1H). HRMS Calculated for [C14H24N2O2+H]+: 253.1916. Found: 253.1925

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