反应详情

To a solution of 1-allyloxycarbonyl-3-hydroxymethylpyrrolidine (2.6 g) in acetone was added Jones reagent (1.25N, 20 ml) at ambient temperature. After stirring for 1 hour, isopropyl alcohol (10 ml) was added thereto. The resulting precipitate was removed by filtration and the filtrate was evaporated in vacuo. The residue was dissolved in dichloromethane, dicyclohexylcarbodiimide (0.79 g), Meldrum's acid (0.55 g), 4-methylaminopyridine (0.47 g) to the solution at 0° C. After stirring for 24 hours at ambient temperature, the resulting precipitate was removed by filtration. The filtrate was washed with 1N hydrochloric acid and evaporated in vacuo. The residue was dissolved in a mixture of acetic acid (10 ml) and water (7 ml), and the mixture was refluxed for 1 hour. Evaporation of the solvent gave a residue, which was taken up into ethyl acetate. The solution was washed in turn with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (2:1, V/V) to give 3-acetyl-1-allyloxycarbonylpyrrolidine (2.01 g).

1. customThe resulting precipitate was removed by filtration
2. customthe filtrate was evaporated in vacuo
3. dissolutionThe residue was dissolved in dichloromethane
4. customat 0° C
5. stirringAfter stirring for 24 hours at ambient temperature
6. customthe resulting precipitate was removed by filtration
7. washThe filtrate was washed with 1N hydrochloric acid
8. customevaporated in vacuo
9. dissolutionThe residue was dissolved in a mixture of acetic acid (10 ml) and water (7 ml)
10. temperaturethe mixture was refluxed for 1 hour
11. customEvaporation of the solvent
12. customgave a residue, which
13. washThe solution was washed in turn with saturated sodium bicarbonate and brine
14. dry with materialdried over magnesium sulfate
15. customevaporated
16. customThe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (2:1, V/V)