Tin dichloride dihydrate → HCID 89628486, compound

Participants

Reaction Steps

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 (25 mg, 0.092 mmol) and tin(II)chloride hydrate (83 mg, 0.369 mmol) was heated in methanol (15 mL) for 2 hours. The reaction mixture was cooled to room temperature, concentrated to dryness, and re-dissolved in ethyl acetate (20 mL). The organic solution was washed with sat. NaHCO3 solution (5 mL), brine (5 mL), dried (MgSO4), and concentrated. Purification by column chromatography (4 g, SiO2, 0 to 5% chloroform/methanol/ammonium hydroxide 80:18:2 in dichloromethane) provided (E)-5-(3-(2-aminophenyl)acryloyl)-3-isobutyl-3-phenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one as a white solid: 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 0.83-1.01 (m, 6H), 1.62-1.75 (m, 1H), 1.84 (dd, J=14.69, 7.16 Hz, 1H), 2.35 (dd, J=14.69, 4.52 Hz, 1H), 2.43-2.55 (m, 2H), 3.51 (m, J=5.70 Hz, 1H), 3.82-4.00 (m, 3H), 4.09 (d, J=19.59 Hz, 1H), 4.84 (d, J=19.21 Hz, 1H), 6.66-6.86 (m, 3H), 7.18 (t, J=7.54 Hz, 1H), 7.29-7.48 (m, 6H), 7.83 (d, J=15.07 Hz, 1H); MS m/z 417 (M+H)+, 439 (M+23)+, 415 (M−H)−.

Provenance & Evidence