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

Participants

Reaction Steps

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.

Provenance & Evidence