1-Phenylcyclopentanecarboxylic acid → N-[(3aS*,4R*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-1-phenylcyclopentanecarboxamide

HRID 1092467Notes

Reaction equation

HRID 1092467 reaction equation
ON1C2C=CC=CC=2N=N1.CC[N+](CCCN(C)C)=C=N.[C:22]1([C:28]2([C:33]([OH:35])=O)[CH2:32][CH2:31][CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH2:36]([N:43]1[CH2:47][C@H:46]2[CH:48]([NH2:51])[CH2:49][CH2:50][C@H:45]2[CH2:44]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl>[CH2:36]([N:43]1[CH2:47][C@H:46]2[C@H:48]([NH:51][C:33]([C:28]3([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:29][CH2:30][CH2:31][CH2:32]3)=[O:35])[CH2:49][CH2:50][C@H:45]2[CH2:44]1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 661671-Phenylcyclopentanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 218833923-(Dimethylamino)propyl-ethyl-(iminomethylidene)azaniumHCID 68411161(3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 46213302N-[(3aS*,4R*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-1-phenylcyclopentanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Hydroxybenzotriazole (33 mg, 0.24 mmol) and N-(3-dimethylaminopropyl)-N-ethylcarbodiimide (43 μL, 0.24 mmol) were added to a solution of 1-phenylcyclopentanecarboxylic acid (46 mg, 0.24 mmol) in dichloromethane (2 mL). The reaction was stirred at room temperature for 10 minutes, then (3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine (52 mg, 0.24 mmol) was added and the reaction stirred at room temperature overnight. The reaction was quenched with water, and extracted with dichloromethane, then purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/chloroform as eluent to give the title compounds.

Workup

  1. stirringthe reaction stirred at room temperature overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with dichloromethane
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-c303e915df6748728df1d3036287334a
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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