Diisopropylethylamine → ethyl 4-cyclohexyl-1-[(R)-2-isothiocyanato-3-(4-methoxyphenyl)propionyl]piperidine-4-carboxylate

Participants

Reaction Steps

To 500 mg (0.94 mmol) of ethyl 1-[(R)-2-amino-3-(4-methoxyphenyl)propionyl]-4-cyclohexylpiperidine-4-carboxylate trifluoroacetate dissolved in 5 mL of CH2Cl2 and 0.5 mL (2.8 mmol) of diisopropylethylamine are added 219 mg (0.94 mmol) of thiocarbonic acid O,O-bis(2-pyridyl)ester. After stirring the reaction medium for 2 hours at room temperature, the solvents are evaporated off and the crude product obtained is chromatographed on silica gel (eluent: 6/4 heptane/EtOAc). 421 mg of ethyl 4-cyclohexyl-1-[(R)-2-isothiocyanato-3-(4-methoxyphenyl)propionyl]piperidine-4-carboxylate in the form of a colourless oil are obtained in a yield of 97%.

Provenance & Evidence