Pyridine → Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate

Participants

Reaction Steps

To a mixture of ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate (11.5 g), ethyl acetate (200 ml) and pyridine (12 g) is added thionyl chloride (5 ml), and the resulting mixture is refluxed for 1 hour with stirring. After cooling, the mixture is diluted with water (500 ml) and ethyl acetate (100 ml). The organic layer is separated, washed successively with 0.1N hydrochloric acid and water, dried over anhydrous magnesium sulfate, treated with activated carbon and then evaporated in vacuo to give ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate (10.5 g) as a pale yellow oil.

Provenance & Evidence