反应详情

温度

0 °C

1,2,3,3a,8,8a-Hexahydro-5-nitro-1,3a,8-trimethylpyrrolo[2,3-b]indole (2.2 g) was dissolved in ethyl acetate (100 ml) and hydrogenated in a Parr apparatus at 45 psi using PtO2 (220 mg) as a catalyst. The reduction was complete within 2 hours. The reduction mixture was filtered directly into a nitrogen flushed flask. 4-Dimethylaminopyridine (0.100 g) and triethylamine (0.9 g) were added, the mixture was cooled to 0° C. and a solution of benzylchloroformate (1.5 g) in ethyl acetate (100 ml) was added over a period of 1.5 hours. The mixture was washed with water (2×100 ml), dried (Na2SO4), concentrated and purified by flash chromatography on silica gel (eluting with 15% MeOH/EtOAc). The pure fractions were concentrated to give 5-(benzoxycarbonylamino)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo-[2,3-b]indole (1.2 g).

1. filtrationThe reduction mixture was filtered directly into a nitrogen flushed flask
2. addition4-Dimethylaminopyridine (0.100 g) and triethylamine (0.9 g) were added
3. additiona solution of benzylchloroformate (1.5 g) in ethyl acetate (100 ml) was added over a period of 1.5 hours
4. washThe mixture was washed with water (2×100 ml)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. custompurified by flash chromatography on silica gel (eluting with 15% MeOH/EtOAc)
8. concentrationThe pure fractions were concentrated