1,2-Dimethoxyethane → Tert-butyl 4-cyanopiperidine-1-carboxylate

Participants

Reaction Steps

1-tert-Butyloxycarbonyl-4-piperidone (13 g) and p-toluenesulfonylmethylisocyanate (16.6 g) were added to 1,2-dimethoxyethane (90 ml) and ethanol (10 ml). The solution was cooled in ice, potassium tert-butoxide (8.3 g) was added thereto under stirring and the mixture was stirred at room temperature for 6.5 hours. Water was added to the reaction solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo and the resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 4-cyanopiperidine-1-carboxylic acid tert-butyl ester (8.0 g) as a solid.

Provenance & Evidence