1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[(3aS*,4R*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-1-phenylcyclopentanecarboxamide

HRID 2363439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2363439
ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[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

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 661671-Phenylcyclopentanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 68411161(3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 mixture 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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1c05f183e5ac43f0829a366ef35e84d8
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691865B2

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