Iodoethane → 3-Ethyl-1-(4-fluorobenzoyl)-2-oxopyrrolidine-3-carbonitrile
Reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([N:8]2[CH2:12][CH2:11][CH:10]([C:13]#[N:14])[C:9]2=[O:15])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:21][CH3:22].[Cl-].[NH4+]>CN(C)C=O>[CH2:21]([C:10]1([C:13]#[N:14])[CH2:11][CH2:12][N:8]([C:6](=[O:7])[C:5]2[CH:16]=[CH:17][C:2]([F:1])=[CH:3][CH:4]=2)[C:9]1=[O:15])[CH3:22]Participants
Procedure
To a solution of 1-(4-fluorobenzoyl)-2-oxopyrrolidine-3-carbonitrile (1.3 g) obtained in Step F in N,N-dimethylformamide (10 mL) was added sodium hydride (60% in mineral oil, 340 mg) in an ice bath, and the mixture was stirred at the same temperature for 30 min. To the reaction mixture was added dropwise iodoethane (0.90 mL) in an ice bath, and the mixture was stirred at the same temperature for 30 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.1 g).
Workup
- stirringthe mixture was stirred at the same temperature for 30 min
- extractionthe mixture was extracted with ethyl acetate
- washThe obtained organic layer was washed successively with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-c41da7db10a84fab917267476631785d
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187453B2
Reaction notes
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