Water → Ethyl 1-benzyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

HRID 477042Notes

Reaction equation

HRID 477042 reaction equation
Cl[C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[CH:7]=O.[CH2:9]([O:11][C:12](=[O:22])[CH2:13][NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:10].O>C1(C)C=CC=CC=1>[CH2:15]([N:14]1[C:13]([C:12]([O:11][CH2:9][CH3:10])=[O:22])=[CH:7][C:3]2[CH2:4][CH2:5][CH2:6][C:2]1=2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 80908N-Benzylglycine ethyl esterHCID 123899702-Chlorocyclopent-1-ene-1-carbaldehyde

Product 1

HCID 13592288Ethyl 1-benzyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

46.7 g (0.358 mol) of 2-chloro-1-formylcyclopent-1-ene are dissolved in 400 ml of toluene. 138 g (0.716 mol) of N-benzylglycine ethyl ester are added. The mixture is refluxed for one hour, the water of reaction being separated off via a water separator. After cooling, any precipitate formed is filtered off with suction and the toluene solution is washed with water, dried and concentrated. The residue is taken up in 300 ml of ethanol, 600 ml of 2N hydrochloric acid are added and the mixture is extracted 3× with petroleum ether. The petroleum ether phase is washed with 2×175 ml of ethanol/2N hydrochloric acid 1:2 and then with 100 ml of saturated NaHCO3 solution, the organic phase is dried over MgSO4, stirred with active charcoal and filtered with suction, and the filtrate is evaporated in vacuo. Yield: 53.1 g of oil.

Workup

  1. temperatureThe mixture is refluxed for one hour
  2. custombeing separated off via a water separator
  3. temperatureAfter cooling
  4. customany precipitate formed
  5. filtrationis filtered off with suction
  6. washthe toluene solution is washed with water
  7. customdried
  8. concentrationconcentrated
  9. addition600 ml of 2N hydrochloric acid are added
  10. extractionthe mixture is extracted 3× with petroleum ether
  11. washThe petroleum ether phase is washed with 2×175 ml of ethanol/2N hydrochloric acid 1:2
  12. dry with materialwith 100 ml of saturated NaHCO3 solution, the organic phase is dried over MgSO4
  13. filtrationfiltered with suction
  14. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-4eabbe1a968a4c12aabf8716298bed40
Source dataset
uspto-grants-1989_12
Patent number
US04886827

Reaction notes

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