反应详情

A −20° C. suspension of Example 1E (400 mg, 1.56 mmol) in dichloromethane (10 mL) and THF (10 mL) was treated with formic acetic anhydride (0.135 mL, 1.7 mmol), stirred for 1 hour, and concentrated. The concentrate was suspended in benzene (50 mL), treated with 65% Red-Al in toluene (2.4 mL, 7.8 mmol), stirred at room temperature for 20 minutes than heated to reflux for 6 hours. The reaction was cooled to room temperature and partitioned between Rochelle's salt and ethyl acetate. The aqueous phase was extracted three times with ethyl acetate and the combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 7% methanol/dichloromethane to provide the desired product (86 mg). MS(ESI(+)) m/e 271 (M+H)+.

1. concentrationconcentrated
2. stirringstirred at room temperature for 20 minutes
3. temperaturethan heated
4. temperatureto reflux for 6 hours
5. custompartitioned between Rochelle's salt and ethyl acetate
6. extractionThe aqueous phase was extracted three times with ethyl acetate
7. washthe combined extracts were washed with water and brine
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe concentrate was purified by flash column chromatography on silica gel with 7% methanol/dichloromethane