反应详情

To a solution of trans-4,6,6a,7,9,10a-hexahydro-7-methyl-10a-methyl-1-methoxy-4-(2,4,6-triisopropylphenylsulfonyl)-indolo[3,4-gh][1,4]benzoxazin-8-one (1.9 g, 3.4 mmol) in THF (30 ml) was added, while stirring under ice-cooling, LAH (3 equivalents). The mixture was heated for 3 hours under reflux. After completion of the reaction, ethanol was added to the reaction mixture, and the mixture was then added to an ice-cooled saturated aqueous solution of sodium sulfate. The mixture was subjected to extraction with ethyl acetate. The extract was washed with an aqueous saline solution, and was then dried (anhydrous sodium sulfate). The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography, eluting with ethyl acetate to leave 700 mg of a residual substance. To a solution of this residual substance in THF (10 ml) was added, at room temperature in argon streams, a solution of 0.5M naphthalene sodium in THF (10 equivalents). The mixture was stirred for 10 minutes at room temperature, and was added to an ice-cooled saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saline solution, which was dried (anhydrous sodium sulfate). The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography, eluting with ethyl acetate to afford 250 mg (27%) of the title compound as crystals, m.p.200°-202° C. (isopropyl ether-ethyl acetate).

1. temperaturecooling
2. temperatureThe mixture was heated for 3 hours
3. temperatureunder reflux
4. additionwas added to the reaction mixture
5. extractionThe mixture was subjected to extraction with ethyl acetate
6. washThe extract was washed with an aqueous saline solution
7. dry with materialwas then dried (anhydrous sodium sulfate)
8. distillationThe solvent was distilled off under reduced pressure
9. washeluting with ethyl acetate
10. customto leave 700 mg of a residual substance
11. stirringThe mixture was stirred for 10 minutes at room temperature
12. extractionfollowed by extraction with ethyl acetate
13. washThe organic layer was washed with an aqueous saline solution, which
14. dry with materialwas dried (anhydrous sodium sulfate)
15. distillationThe solvent was distilled off under reduced pressure
16. washeluting with ethyl acetate