HCID 71610394, compound → HCID 71610395, compound

Participants

Reaction Steps

To a solution of (E)-3-isobutyl-5-(3-(2-nitrophenyl)acryloyl)-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (90 mg, 0.20 mmol) in ethanol/ethyl acetate/(3:1, 20 mL) was added Pd/C (10%, 20 mg). The reaction mixture was stirred vigorously under an atmosphere of H2(g) at room temperature for 1 h. The mixture was filtered through a pad of diatomaceous earth, the filtrate concentrated in vacuo, and the residue purified by column chromatography (4 g, SiO2, 0 to 50% ethyl acetate in hexanes) to provide 5-(3-(2-aminophenyl)propanoyl)-3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (54 mg, 64%): 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.82-0.98 (m, 6H), 1.59-1.71 (m, 1H), 1.73-1.87 (m, 1H), 2.18-2.37 (m, 2H), 2.72 (d, J=6.78 Hz, 2H), 2.87 (d, J=6.78 Hz, 2H), 3.22-3.33 (m, 1H), 3.46-3.66 (m, 2H), 3.77-3.89 (m, 2H), 3.92-4.04 (m, 1H), 4.60-4.74 (m, 1H), 6.59-6.64 (m, 2H), 6.96-7.07 (m, 2H), 7.28-7.44 (m, 5H); MS m/z 419 (M+H)+.

Provenance & Evidence