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]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- stirringthe reaction stirred at room temperature overnight
- customThe reaction was quenched with water
- extractionextracted with dichloromethane
- custompurified by silica gel chromatography
Sources & evidence
- ORD record
- ord-c303e915df6748728df1d3036287334a
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129417B2
Linked notes
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