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

HRID 1762290Notes

Reaction equation

HRID 1762290 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, ooncentrate 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. customooncentrate under high vacuum to obtain a brown oil
  9. distillationdistill in a kugelrohr at 190°-210°/0.1 mm

Sources & evidence

ORD record
ord-ebb01ef61b3a41e99c36613a9f7b9272
Source dataset
uspto-grants-1989_05
Patent number
US04831157

Reaction notes

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