Acetonitrile → 1-Benzyl-3-methylpyrrolidine-3-carbonitrile

HRID 622379Notes

Reaction equation

HRID 622379 reaction equation
[CH2:1](N(CC#N)C[Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](#[N:21])[C:18]([CH3:20])=[CH2:19].[C:22](#[N:24])C.[C:25](OCC)(=O)C>C(Cl)(Cl)Cl.[Ag]F>[CH3:19][C:18]1([C:22]#[N:24])[CH2:20][CH2:25][N:21]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 31368MethacrylonitrileHCID 560960N-Benzyl-N-(trimethylsilylmethyl)aminoacetonitrile

Product 1

HCID 50864491-Benzyl-3-methylpyrrolidine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 62656Caswell No. 736CatalystHCID 6212ChloroformSolvent2×

Procedure

A suspension of 11.6 g (0.05 mole) of N-benzyl-N-(cyanomethyl)-N-[(trimethylsilyl)methyl]amine [J. Org. Chem., 50, 4006 (1985)], 3.5 g (0.052 mole) of methacrylonitrile, 7.0 g (0.55 mole) of silver fluoride, and 150 ml of acetonitrile was stirred overnight at room temperature in the dark. The mixture was then diluted with chloroform (150 ml) and filtered through Celite. Concentration of the filtrate gave an oil which was subjected to silica gel chromatography using an 80:20 chloroform:ethyl acetate mixture as the eluent. The major fraction contained 2.5 g of the titled compound.

Workup

  1. filtrationfiltered through Celite
  2. customConcentration of the filtrate gave an oil which

Sources & evidence

ORD record
ord-eefa92c9b3ea45d0abd3712bad8c3c76
Source dataset
uspto-grants-1988_09
Patent number
US04771055

Reaction notes

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