Ethyl Acrylate → Ethyl 1-(3-ethoxy-3-oxopropyl)pyrrolidine-3-carboxylate

HRID 2379420Notes

Reaction equation

HRID 2379420 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].[C:22]([O:26][CH2:27][CH3:28])(=[O:25])[CH:23]=[CH2:24]>C(O)C.[Pd]>[CH2:27]([O:26][C:22]([CH2:23][CH2:24][N:8]1[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9]1)=[O:25])[CH3:28]

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 2723923Ammonium formateHCID 11622765Ethyl 1-benzylpyrrolidine-3-carboxylate

Product 1

HCID 18957099Ethyl 1-(3-ethoxy-3-oxopropyl)pyrrolidine-3-carboxylateYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0f4e98fca78e403c8ea2a752d23f2d15
Source dataset
uspto-grants-1994_11
Patent number
US05362739

Reaction notes

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