Hydrochloric Acid → 3-(4-fluorophenyl)-3-isobutyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(4-fluorophenyl)-3-isobutylfuro[3,4-c]pyridin-1(3H)-one (296 mg, 1.04 mmol) in dichloromethane (5 mL) at 0° C. was added 1 N HCl in diethyl ether. The reaction mixture was stirred at 0° C. for 40 min., then filtered and the precipitated hydrochloride salt dried in high vacuo for 1 hour. The precipitate was re-dissolved in ethanol (10 mL), PtO2 (40 mg) was added, and the reaction mixture was hydrogenated at 40 psi for 30 min. The mixture was filtered through a pad of diatomaceous earth, the filtrate concentrated in vacuo. The residue was re-dissolved in dichloromethane (50 mL) and stirred with sat. NaHCO3 soln. for 20 min., then dried (MgSO4) and concentrated. The residue was purified by column chromatography (4 g, SiO2, 0 to 2.5% methanol in dichloromethane) to provide 3-(4-fluorophenyl)-3-isobutyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (160 mg, 53%): 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.83-0.98 (m, 6H), 1.56 (br. s., 1H), 1.65 (ddd, J=13.37, 6.59, 5.27 Hz, 1H), 1.72-1.81 (m, 1H), 2.15-2.38 (m, 3H), 2.84-3.05 (m, 2H), 3.34-3.50 (m, 1H), 3.58-3.73 (m, 1H), 7.00-7.12 (m, 2H), 7.27-7.34 (m, 2H); MS m/z 290 (M+H)+, 288 (M−H)−.

Provenance & Evidence