Hydrogen Bromide → HCID 46938317, compound

Participants

Reaction Steps

(2S,4R)-Methyl 2-(5-tert-butylthiophen-2-yl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (50 mg, 0.14 mmol) (from example 42, step 3) was dissolved in hydrobromic acid (33% in AcOH, 1 mL, 6.08 mmol) and stirred at room temperature for 20 h. The solvent was evaporated in vacuo. The compound was purified by preparative HPLC on a XBridge C18 column (10 μm 250×19 ID mm) using a gradient of 10-50% Acetonitrile in H2O/MeCN/NH3 95/5/0.2 buffer over 25 minutes with a flow of 19 mL/min. 5-((2S,4R)-2-(5-tert-Butylthiophen-2-yl)piperidin-4-yl)isoxazol-3(2H)-one (7.00 mg, 16.65%) was isolated as a white solid. 1H NMR (600 MHz, cd3od) δ 1.36 (s, 9H), 2.03-2.12 (m, 1H), 2.12-2.19 (m, 1H), 2.26-2.33 (m, 1H), 2.40-2.46 (m, 1H), 3.09-3.17 (m, 1H), 3.18-3.24 (m, 1H), 3.34-3.40 (m, 1H), 4.38-4.44 (m, 1H), 5.75 (s, 1H), 6.78 (d, 1H), 6.96 (d, 1H).

Provenance & Evidence