2-Naphthoyl chloride → 5-(2-naphthoyl)-3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (50 mg, 0.184 mmol) and N,N′-diisopropylethylamine (71 mg, 0.552 mmol) in THF (5 mL) at 0° C. was added 2-naphthoylchloride (35 mg, 0.184 mmol) and the reaction mixture was stirred at 0° C. for 30 min, then room temperature overnight. The crude mixture was concentrated to dryness and purified by column chromatography (4 g, SiO2, 0 to 30% ethyl acetate in hexanes) to provide 5-(2-naphthoyl)-3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (68 mg, 87%) as a white solid: 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.77-1.08 (m, 6H), 1.63-1.78 (m, 1H), 1.79-1.95 (m, 1H), 2.28-2.59 (m, 3H), 3.28-3.60 (m, 1H), 3.73 (br. s., 1H), 4.09-4.27 (m, 1H), 4.85 (br. s., 1H), 7.29-7.51 (m, 6H), 7.52-7.62 (m, 2H), 7.77-7.98 (m, 4H); MS m/z 426 (M+H)+, 449 (M+23)+, 424 (M−H)−.

Provenance & Evidence