反应详情

温度

70 °C

A solution of (±) ethyl N-benzyl-3-pyrrolidinyl carboxylate (D1) (100 g, 0.43 mole) in ethanol (800 ml) was treated with ammonium formate (135.32 g, 2.15 mole) and 10% Pd on carbon (25 g) then heated at 70° C. for 2h. After 1h a further addition of 10% Pd on carbon (10 g) was made. The reaction mixture was filtered through celite and the filtrate concentrated in vacuo. The residue was partitioned between chloroform and saturated aqueous potassium carbonate solution. The organic phase was separated, dried (Na2SO4), and concentrated in vacuo. The residue was dissolved in ethanol (500 ml), treated with ethyl acrylate (51.56 g, 0.52 mole) then heated under reflux for 1h. The reaction mixture was concentrated in vacuo, treated with saturated aqueous potassium carbonate, then extracted into chloroform. The combined organic extracts were dried (Na2SO4), concentrated in vacuo and the residue distilled to afford the title compound (D2) as an oil (60.53 g, 58%), b.p. 135°-145° C. at 4 mmHg.

1. filtrationThe reaction mixture was filtered through celite
2. concentrationthe filtrate concentrated in vacuo
3. customThe residue was partitioned between chloroform and saturated aqueous potassium carbonate solution
4. customThe organic phase was separated
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in ethanol (500 ml)
8. temperaturethen heated
9. temperatureunder reflux for 1h
10. concentrationThe reaction mixture was concentrated in vacuo
11. additiontreated with saturated aqueous potassium carbonate
12. extractionextracted into chloroform
13. dry with materialThe combined organic extracts were dried (Na2SO4)
14. concentrationconcentrated in vacuo
15. distillationthe residue distilled