反应详情

温度

50 °C

A solution containing the product from Example 3G (1.304 g, 5.66 mmol) in a mixture of benzene (15 mL) and methanol (15 mL) was treated with the product from Example 97A (1.05 g, 6.79 mmol), was heated at 50° C. for 3 hours, cooled to 0° C., treated with sodium borohydride (0.428 g, 11.32 mmol), stirred at 25° C. for 16 hours, quenched with sodium bicarbonate solution, and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the concentrate (5.66 mmol) in toluene (30 mL) was treated with bis(4-nitrophenyl)carbonate (2.066 g, 6.79 mmol), heated at 100° C. for 16 hours, cooled and partitioned between ethyl acetate and saturated NaHCO3. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-25% ethyl acetate in dichloromethane to give the title compound (1.68 g, 75% yield).

1. temperaturecooled to 0° 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. concentrationA solution of the concentrate (5.66 mmol) in toluene (30 mL)
9. temperatureheated at 100° C. for 16 hours
10. temperaturecooled
11. custompartitioned between ethyl acetate and saturated NaHCO3
12. washThe organic phase was washed with brine
13. dry with materialdried over MgSO4
14. filtrationfiltered
15. concentrationconcentrated
16. customThe residue was chromatographed on silica gel eluting with 0-25% ethyl acetate in dichloromethane