反应详情

A mixture of methyl (1aRS,7bSR)-5-[N-(methoxycarbonyl)-N-(4-fluoro-2-nitrobenzene-sulfonyl)amino]-1,1a,2,7b-tetrahydro-cyclopropa[c]chromene-4-carboxylate (Intermediate 111, 0.2 g), zinc (0.54 g) and acetic acid (0.5 g) in ethanol (20 mL) was stirred and heated at reflux for 1 hour. After cooling, the solid was filtered off and the filtrate was evaporated to dryness. The residue was treated with saturated aqueous sodium bicarbonate and extracted with ethyl acetate, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and petroleum ether with a gradient of 30-50% to give methyl (1aRS,7bSR)-5-[N-(methoxycarbonyl)-N-(2-amino-4-fluorobenzenesulfonyl)amino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (0.15 g) as a white solid.

1. temperatureheated
2. temperatureat reflux for 1 hour
3. temperatureAfter cooling
4. filtrationthe solid was filtered off
5. customthe filtrate was evaporated to dryness
6. additionThe residue was treated with saturated aqueous sodium bicarbonate
7. extractionextracted with ethyl acetate
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. customThe filtrate was evaporated to dryness
11. customthe residue was purified by chromatography on silica
12. washeluting with a mixture of ethyl acetate and petroleum ether with a gradient of 30-50%