Water → Tert-butyl 4-(1-cyano-2-oxoethyl)piperidine-1-carboxylate

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Reaction Steps

Under an argon atmosphere, tert-butyl 4-(cyanomethyl)piperidine-1-carboxylate (2.24 g, 10 mmol) and potassium tert-butoxide (6.73 g, 60 mmol) were dissolved in anhydrous N,N-dimethyl formamide (15 mL), and a solution of ethyl formate (4.44 g, 60 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added dropwise under ice-cooling. The temperature was gradually raised to room temperature, and then the resultant mixture was stirred overnight. Water was added to the reaction liquid, followed by extraction with ethyl acetate. 1 N hydrochloric acid was added to the obtained aqueous layer until it reached a pH of 6, and then the resultant mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure to give tert-butyl 4-(1-cyano-2-oxoethyl)piperidine-1-carboxylate (2.35 g) as a crude product.

Provenance & Evidence