反应详情

To a suspension of methyltriphenylphosphonium bromide (1.07 g) was portionwise added potassium t-butoxide (337 mg) with stirring under ice-cooling. The mixture was stirred at ambient temperature for 2 hours. To the solution cooled on ice-bath was added dropwise (2S,4R)-1-benzyl-2-formyl-4-(t-butyldimethylsilyloxy)pyrrolidine (0.92 g) in toluene (2 ml) and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was poured into a mixture of water (10 ml) and ethyl acetate (20 ml). The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo to give a residue. To the residue was added n-hexane (30 ml). The resulting precipitates were filtered off and the filtrate was evaporated in vacuo. The resulting residue was chromatographed on silica gel (1 g) eluting with a mixture of n-hexane and ethyl acetate (5:1 v/v). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-1-benzyl-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine (765 mg).

1. temperaturecooling
2. stirringThe mixture was stirred at ambient temperature for 2 hours
3. temperatureTo the solution cooled on ice-bath
4. stirringthe mixture was stirred at the same temperature for 1 hour
5. customThe organic layer was separated
6. washwashed with saturated aqueous sodium chloride
7. dry with materialdried over anhydrous magnesium sulfate
8. customevaporated in vacuo
9. customto give a residue
10. customThe resulting precipitates
11. filtrationwere filtered off
12. customthe filtrate was evaporated in vacuo
13. customThe resulting residue was chromatographed on silica gel (1 g)
14. washeluting with a mixture of n-hexane and ethyl acetate (5:1 v/v)
15. additionThe fractions containing the desired compound
16. customwere collected
17. customevaporated in vacuo