1,2-Dichloroethane → 2-Methyl-6-oxo-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid benzylamide

HRID 2213558Notes

Reaction equation

HRID 2213558 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[C:7](=[O:10])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([OH:13])=O.[CH:14]1[CH:15]=[CH:16][C:17]2N(O)N=N[C:18]=2[CH:19]=1.C(Cl)CCl.[NH2:28][C:29]1C=CC=CC=1>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+].O>[CH2:29]([NH:28][C:11]([C:3]1[C:4]2[CH2:9][CH2:8][C:7](=[O:10])[C:5]=2[NH:6][C:2]=1[CH3:1])=[O:13])[C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:19]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 219575932-Methyl-6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-3-carboxylic acid

Product 1

HCID 210515532-Methyl-6-oxo-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid benzylamideYield 78.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 2-methyl-6-oxo-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid (Example B, 268.5 mg, 1.5 mmol), HOBt (202.5 mg, 1.5 mmol) and EDC (573.5 mg, 3 mmol) in dry DMF (5 mL) was stirred at room temperature for 20 min. Then aniline (3.0 mmol) was added to the mixture and stirring was continued for 24 hours. The reaction was diluted with sat. Na2CO3 and water, the solid was collected by vacuum filtration, washed with sat. Na2CO3 and water in turn, dried to give 315 mg of the titled compound as a white solid.

Workup

  1. stirringstirring
  2. waitwas continued for 24 hours
  3. filtrationthe solid was collected by vacuum filtration
  4. washwashed with sat. Na2CO3 and water in turn
  5. customdried

Sources & evidence

ORD record
ord-12a6b5ef39fd42db8d9d0184fa36b396
Source dataset
uspto-grants-2006_09
Patent number
US07105562B2

Reaction notes

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