Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 7-(2-Chloroethoxy)-alpha-(cyclohexylthio)-alpha-(3,4-dimethoxyphenyl)-3,4-dihydro-6-methoxy-2(1H)-isoquinolineheptanonitrile

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Reaction Steps

A mixture, under argon, of 2.0 g of product from Example 114, 15 ml of 1N sodium hydroxide, 5.4 ml of 2-chloroethyl-p-toluene sulfonate and 70 ml of 2-butanone is heated at reflux temperature for 18 hours. The mixture is cooled, concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic layer is washed with saturated sodium chloride, dried, and concentrated in Vacuo to give an oil. The oil is purified by chromatography (silica gel: methylene chloride, 0.5%, 1.0% and 1.5% methyl alcohol/methylene chloride) to give 1.7 g of the desired product.

Provenance & Evidence