反应详情

温度

-78 °C

(5R,6S)-1-((S)-1-(Tert-butyldiphenylsilyloxy)butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)piperidin-2-one (1.100 g, 1.744 mmol; Example 185, Step C) was dissolved in THF (8.72 mL) and sparged with argon for 5 minutes. The mixture was cooled to −78° C. and 1.0 M lithium bis(trimethylsilyl)amide solution in THF (2.093 mL, 2.093 mmol) was added dropwise. After 30 minutes, peroxybis(trimethylsilane) (0.413 mL, 1.918 mmol) was added dropwise. After 1 hour, the cooling bath was removed. After stirring overnight, the mixture was quenched with sat. aq. NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with sat. aq. NaCl solution, dried over Na2SO4, and concentrated. The residue was dissolved in EtOH (14 mL) and pyridine p-toluenesulfonate (131 mg, 0.523 mmol) was added. After 1 hour, the mixture was basified with sat. aq. NaHCO3 solution. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with sat. aq. NaCl solution, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography on silica gel (40 g column, eluent: 5 to 50% ethylacetate/hexanes) to afford the title compound.

1. customsparged with argon for 5 minutes
2. waitAfter 1 hour
3. customthe cooling bath was removed
4. customthe mixture was quenched with sat. aq. NH4Cl solution
5. extractionextracted with ethyl acetate
6. washThe organic layer was washed with sat. aq. NaCl solution
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. dissolutionThe residue was dissolved in EtOH (14 mL)
10. waitAfter 1 hour
11. customThe mixture was partitioned between ethyl acetate and water
12. washThe organic layer was washed with sat. aq. NaCl solution
13. dry with materialdried over Na2SO4
14. concentrationconcentrated
15. customThe residue was purified by flash chromatography on silica gel (40 g column, eluent: 5 to 50% ethylacetate/hexanes)