N-Benzylglycine ethyl ester → Ethyl 1-benzyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate

HRID 477043Notes

Reaction equation

HRID 477043 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]>>[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

3

Reactant 2

HCID 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

Conditions

Temperature
110 °C

Procedure

25 g (0.191 mol) of 2-chloro-1-formylcyclopent-1-ene are added to 73.9 g (0.382 mol) of N-benzylglycine ethyl ester at room temperature and the mixture is then heated to 110° C. Working-up is carried out as indicated in Example 1.

Sources & evidence

ORD record
ord-9fb186bfd885412e9d8c59dc2f79687d
Source dataset
uspto-grants-1989_12
Patent number
US04886827

Reaction notes

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