Ethyl Acetate → 5-cinnamoyl-3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one

Participants

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) in THF (5 mL) was added trans-cinnamaldehyde (49 mg, 0.369 mmol) and the reaction mixture stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (117 mg, 0.553 mmol) was added and the reaction mixture stirred at room temperature for additional 2 hours. Ethyl acetate (10 mL) was added and the organic solution washed with sat. NaHCO3 (10 mL), brine (10 mL), dried (MgSO4), and concentrated. The residue was purified by column chromatography (12 g, SiO2, 0 to 20% ethyl acetate in hexanes) to provide 5-cinnamoyl-3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (45 mg, 63%) as a white solid: 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.73-1.05 (m, 6H), 1.54-1.84 (m, 2H), 2.20-2.48 (m, 3H), 2.52-2.66 (m, 1H), 2.73-2.89 (m, 1H), 2.99-3.14 (m, 1H), 3.19-3.37 (m, 2H), 3.43 (d, J=17.71 Hz, 1H), 6.23 (dt, J=15.82, 6.59 Hz, 1H), 6.44-6.57 (m, 1H), 7.20-7.46 (m, 10H); MS m/z 388 (M+H)+, 410 (M+23)+, 386 (M−H)−.

Provenance & Evidence