Piperidine → Methyl 1-methylcyclohexanecarboxylate

Participants

Reaction Steps

Sodium hydrogen carbonate (1.68 g, 20.0 mmol) was added to a solution of trans-4-aminomethyl cyclohexanecarboxylic acid methyl ester hydrochloride (2.07 g, 10.0 mmol) obtained in Step 1, 9-fluorenylmethoxycarbonyl isothiocyanate (2.81 g, 10.0 mmol) in chloroform (40 ml) while ice-cooled. The reaction solution was stirred at room temperature for 16 hours, piperidine (5 ml, 50 mmol) was added, and the mixture was stirred at room temperature for further 6 hours. Trans-4-thiouredide methylcyclohexane carboxylic acid methyl ester (1.55 g, 67%) was obtained by concentrating the reaction solution in vacuo and purifying the obtained solid by silica gel column chromatography (ethyl acetate).

Provenance & Evidence