反应详情

To a solution of methyl 4-{[cyclohexyl(2-ethyl-5-formylthiophen-3-yl)methyl]amino}benzoate (400 mg) synthesized above in tetrahydrofuran (10 mL) was added dropwise 1.0M isopropylmagnesium bromide-tetrahydrofuran solution (1.25 mL) at 0° C., and the mixture was stirred for 1 hr under a nitrogen atmosphere. 1.0M Isopropylmagnesium bromide-tetrahydrofuran solution (1.25 mL) was added dropwise again, and the mixture was further stirred at 0° C. for 1 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography (ethyl acetate) to give a yellow oil. To a solution of the obtained oil in methylene chloride (10 mL) was added Dess-Martin reagent (662 mg) at 0° C., and the mixture was stirred for 1 hr. Saturated aqueous sodium sulfite solution was added to quench the reaction, methylene chloride was evaporated using evaporator, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (15% ethyl acetate/hexane) to give the title compound (268 mg, 60%) as a pale-yellow oil.

1. stirringthe mixture was further stirred at 0° C. for 1 hr
2. customto quench
3. customthe reaction
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with saturated brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by NH-silica gel column chromatography (ethyl acetate)
9. customto give a yellow oil
10. stirringthe mixture was stirred for 1 hr
11. customto quench
12. customthe reaction, methylene chloride
13. customwas evaporated
14. customevaporator
15. extractionthe mixture was extracted with ethyl acetate
16. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
17. dry with materialdried over magnesium sulfate
18. concentrationconcentrated under reduced pressure
19. customThe residue was purified by silica gel column chromatography (15% ethyl acetate/hexane)