反应详情

To a solution of (2S,4R)-2-(difluoromethyl)thiomethyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.01 g) and triphenylphosphine (1.1 g) in tetrahydrofuran (20 ml) was added dropwise a solution of diethyl azodicarboxylate (0.66 ml) in tetrahydrofuran (3 ml) at -10° C. to -5° C. with stirring. The mixture was stirred at the same temperature for 30 minutes. To the solution was added thiobenzoic S-acid (0.49 ml) at the same temperature and the mixture was stirred under ice-cooling for 2 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (60 ml). The solution was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The resulting residue was chromatographed on silica gel (100 g) eluting with a mixture of n-hexane and ethyl acetate (3:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-4-benzoylthio-2-(difluoromethyl)thiomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.01 g).

1. stirringThe mixture was stirred at the same temperature for 30 minutes
2. stirringthe mixture was stirred under ice-
3. temperaturecooling for 2 hours
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. dissolutionThe resulting residue was dissolved in ethyl acetate (60 ml)
6. washThe solution was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively
7. dry with materialdried over anhydrous magnesium sulfate
8. customevaporated in vacuo
9. customThe resulting residue was chromatographed on silica gel (100 g)
10. washeluting with a mixture of n-hexane and ethyl acetate (3:1, V/V)
11. additionThe fractions containing the desired compound
12. customwere collected
13. customevaporated in vacuo