Reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][CH:11]([C:13]#[N:14])[CH2:12][CH:7]2[CH2:6]1)=[O:4].I[CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>CN(C)C=O.O>[CH3:1][N:2]([CH3:15])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([C:13]#[N:14])([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:12][CH:7]2[CH2:6]1)=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
5-Cyano-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 12a was dissolved in 30 mL of N,N-dimethylformamide followed by addition of iodo-cyclopentane (5.4 g, 27.5 mmol) and lithium hexamethyldisilazide (27.5 mL, 27.5 mmol) under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was diluted with 10 mL of water and concentrated to remove N,N-dimethylformamide and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 5-cyano-5-cyclopentyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 16a (2.6 g, yield 42%) as a light yellow solid.
Workup
- concentrationconcentrated
- customto remove N,N-dimethylformamide
- extractionextracted with ethyl acetate
- dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-c4db9e08703f41afbb514a26c29d97cc
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415349B2
Linked notes
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