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1,2-Dichloroethane → 2-Methyl-3-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one

HRID 2213559
Notes
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Reaction equation

HRID 2213559 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.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>CN(C=O)C>[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]([N:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 219575932-Methyl-6-oxo-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-3-carboxylic acid

Product 1

HCID 586978542-Methyl-3-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-4,5-dihydro-1H-cyclopenta[b]pyrrol-6-oneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methyl-6-oxo-1,4,5,6-tetrahydro-cyclopenta[b]pyrrole-3-carboxylic acid (Example B, 3.58 g, 20 mmol), HOBt (2.7 g, 20 mmol) and EDC (5.74 g, 30 mmol) in dry DMF (50 mL) was stirred at 0° C. to room temperature for 20 min. Then (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (24 mmol) was added and stirring was continued for 48 hours. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc, washed with sat. Na2CO3, dried, concentrated and purified on a silica gel column to give 5.1 g (81%) of the titled compound as a yellowish foam.

Workup

  1. stirringstirring
  2. waitwas continued for 48 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with sat. Na2CO3
  6. customdried
  7. concentrationconcentrated
  8. custompurified on a silica gel column

Sources & evidence

ORD record
ord-159715445ea846159869f66922c4f0fc
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07105562B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes