tert-Butyl 4-(cyanomethylidene)piperidine-1-carboxylate → tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylate

Participants

Reaction Steps

Add 4-cyanomethylenepiperidine-1-carboxylic acid t-butyl ester (5.39 g, 24.25 mmol) in ethanol (160 mL) to a suspension of 5% palladium on charcoal (0.69 g) in ethanol (20 mL) and hydrogenate at room temperature with agitation at 60 psi for 6 hr. Filter the mixture through celite and evaporate the solvent in vacuo to give 4-cyanomethylpiperidine-1-carboxylic acid t-butyl ester as an oil which solidifies on standing to give a solid (5.43 g, 99.8%). MS (m/z): 247 (M+Na).

Provenance & Evidence