反应详情

To a solution of 2-benzyl-4-oxo-5-carbomethoxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (0.928 g, 2.78 mmol) in dry tetrahydrofuran (5 mL) was added 60% sodium hydride in oil (111 mg). The resulting mixture was stirred at room temperature until gas evolution ceased. A solution of benzyl iodide (0.606. g, 2.78 mmol) in dry tetrahydrofuran (5 mL) was added to the reaction mixture and the resulting solution stirred at room temperature for 60 h. The mixture was diluted with methylene chloride and washed twice with saturated sodium chloride solution. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was triturated with ethyl acetate resulting in a yellow precipitate (163 mg). The filtrate was concentrated in vacuo and chromatographed (silica gel, 5% methanol/95% methylene chloride) to provide an additional 580 mg of the title compound (743 mg total, 63%) as a crystalline solid: mp 198-199° C. 1H NMR (CDCl3) d 7.43 (d, J=7 Hz, 1 H), 7.36 (d, J=8 Hz, 1 H), 7.25 (m, 9 H), 6.95 (m, 2 H), 5.24 (s, 2 H), 4.01 (s, 3 H), 3.78 (m, 4 H), 3.40 (bs, 2 H); MS EI+ m/e 425 (p+1); IR (KBr, cm−1) 1726, 1648, 1449, 1291, 1134, 1107.

1. stirringthe resulting solution stirred at room temperature for 60 h
2. washwashed twice with saturated sodium chloride solution
3. dry with materialThe organic layer was dried (magnesium sulfate)
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was triturated with ethyl acetate resulting in a yellow precipitate (163 mg)
7. concentrationThe filtrate was concentrated in vacuo
8. customchromatographed (silica gel, 5% methanol/95% methylene chloride)