Pyridine → 2-(alpha-Methoxycarbonyl-3,4-dimethoxybenzylidene)-1-methylpyrrolidine

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Reaction Steps

Add a solution of 0.46 g of sodium in 5 ml of methanol dropwise to a mixture of 5.8 g of the title compound of Example 11 and 4.5 g of homoveratric acid ethyl ester in 15 ml of pyridine. Stir the resulting reaction mixture for 2 hours at 60°, and then distil pyridine and alcohol off under a vacuum before extracting the oily residue first with water and subsequently with petroleum ether. Chromatograph thus-extracted residue on a silica gel column with chloroform/methanol (19:1) to obtain eluate with an RF value 0.76. Concentrate the eluate to obtain a yield (10.5% of theory) of the title compound in the form of an oil.

Provenance & Evidence