反应详情

温度

70 °C

A solution containing the product of Example 3G (0.30 g, 1.30 mmol) in a mixture of benzene (3 mL) and ethanol (3 mL) was treated with the product of Example 3J (0.25 g, 1.31 mmol), heated at 70° C. for 16 hours, cooled to 25° C., treated with sodium borohydride (0.15 g, 3.97 mmol), stirred at 25° C. for 3 hours, quenched with sodium bicarbonate solution and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. A solution of the residue (1.3 mmol) in 1,2-dichloroethane (50 mL) was treated with bis(4-nitrophenyl) carbonate (0.425 g, 1.40 mmol) and triethylamine (0.225 ml, 1.83 mmol), heated at 70° C. for 16 hours, and partitioned between ethyl acetate and saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-35% ethyl acetate in dichloromethane to give the title compound (0.214 g, 38% yield).

1. temperaturecooled to 25° C.
2. customquenched with sodium bicarbonate solution
3. custompartitioned between ethyl acetate and water
4. washThe organic phase was washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. temperatureheated at 70° C. for 16 hours
9. custompartitioned between ethyl acetate and saturated NaHCO3
10. washThe organic phase was washed with brine
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated
14. customThe residue was chromatographed on silica gel eluting with 0-35% ethyl acetate in dichloromethane