Methanol → 1-Benzyl 4-methyl piperidine-1,4-dicarboxylate

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Reaction Steps

1-(Benzyloxycarbonyl)piperidine-4-carboxylic acid (48.5 g) in methanol (485 ml) was cooled to 0° C., and thionyl chloride (13.34 ml) was added dropwise. The mixture was then refluxed for 20 minutes (TLC monitoring). When the reaction was complete, the methanol was distilled off and the residue was taken up in water (15 ml) and with ethyl acetate (2×150 ml). The combined organic phases were extracted with water and saturated sodium chloride solution, dried (Na2SO4) and concentrated in vacuo. Yield: 38 g (67%)

Provenance & Evidence