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

HRID 279899Notes

Reaction equation

HRID 279899 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:10]([N:17]=[C:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(O)C>[CH2:10]([N:17]1[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:2][C:19]2[CH2:20][CH2:21][CH2:22][C:18]1=2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66144Ethyl bromopyruvateHCID 12350908N-Benzylcyclopentanimine

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Add dropwise 3.9 gm of ethyl bromopyruvate in 50 ml of ethanol to a flask containing 3.46 gm of benzyliminocyclopentane and 2.0 g of triethylamine in 50 ml of ethanol at 0° C., stir for 2 hours, then heat to reflux for 2 hours. Concentrate the reaction mixture and partition between 1N HCl and ether. Dry the ether extract over magnesium sulfate, filter, concentrate under high vacuum to obtain a brown oil and distill in a kugelrohr at 190°-210°/0.1 mm to obtain the title compound of Part A as a yellow oil.

Workup

  1. temperatureheat
  2. temperatureto reflux for 2 hours
  3. concentrationConcentrate the reaction mixture
  4. custompartition between 1N HCl and ether
  5. dry with materialDry the ether
  6. extractionextract over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under high vacuum
  9. customto obtain a brown oil
  10. distillationdistill in a kugelrohr at 190°-210°/0.1 mm

Sources & evidence

ORD record
ord-e5baf0904c5c4655af14b67a22f0128a
Source dataset
uspto-grants-1986_05
Patent number
US04587258

Reaction notes

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