反应详情

温度

23 °C

A solution of (S)-7,8-dihydro-2,9-dimethoxy-7-methyl-6-phenanthridinol trifluoromethanesulfonate (ester) (12, 3.00 g, 7.40 mmol, 1 equiv) and m-CPBA (5.10 g, 14.9 mmol, 2.00 equiv) in methanol (120 mL) was heated at reflux for 1 h. After cooling to 23° C., the reaction solution was partitioned between 1:1 saturated aqueous sodium bicarbonate solution:saturated aqueous sodium thiosulfate solution (200 mL) and dichloromethane (200 mL). The aqueous layer was separated and extracted further with dichloromethane (2×200 mL). The combined organic layers were dried over sodium sulfate and were concentrated. The residue was purified by flash column chromatography (25% ethyl acetate-hexanes initially, grading to 40% ethyl acetate-hexanes) away from structure 14 to afford (7S,10R)-7,8,9,10-tetrahydro-2,9,9-trimethoxy-7-methyl-6,10-phenanthridinediol 6-(trifluoro-methanesulfonate) (13) as a yellow foam (2.12 g, 63%). ##STR24##

1. temperatureat reflux for 1 h
2. customthe reaction solution was partitioned between 1:1 saturated aqueous sodium bicarbonate solution
3. customThe aqueous layer was separated
4. extractionextracted further with dichloromethane (2×200 mL)
5. dry with materialThe combined organic layers were dried over sodium sulfate
6. concentrationwere concentrated
7. customThe residue was purified by flash column chromatography (25% ethyl acetate-hexanes initially