1-(1,1-Dimethylethyl) 2-ethyl 4-(cyanomethylene)-1,2-piperidinedicarboxylate → ethyl cis-4-cyanomethyl-N-t-butoxycarbonyl-2-piperidinecarboxylate

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Reaction Steps

Ethyl 4-cyanomethylidene-N-t-butoxycarbonyl-2-piperidinecarboxylate (9.00 g, 0.031 mol) was hydrogenated in 140 ml of ethanol with 0.90 g of 5% by weight palladium-on-carbon at room temperature and 60 p.s.i. for 60 minutes. The mixture was filtered through Celite and concentrated under vacuum. High pressure liquid chromatography of the residue provided 8.20 g of ethyl cis-4-cyanomethyl-N-t-butoxycarbonyl-2-piperidinecarboxylate.

Provenance & Evidence