Potassium Iodide → Ethyl 2-(tert-butoxycarbonylamino)-2-cyano-3-[(-)-menthyloxycarbonyl]propionate

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-(tert-butoxycarbonylamino)-2-cyanoacetate (1.20 g, 5.26 mmol) prepared in the same manner as Reference Example 1, acetone (2.3 ml), powdered potassium carbonate (872 mg, 6.31 mmol) and potassium iodide (175 mg, 1.05 mmol) were mixed, a solution of menthyl chloroacetate (1.22 g, 5.26 mmol) dissolved in acetone (1.1 ml) was added dropwise thereto at 10-20° C., and the mixture was stirred at the same temperature overnight. Insoluble materials were removed by filtration, the filtrate was concentrated in vacuo and toluene was added to the residue. The organic layer was washed with water and concentrated in vacuo to give ethyl 2-(tert-butoxycarbonylamino)-2-cyano-3-[(−)menthyloxycarbonyl]propionate (1.10 g, yield 49.3%) as a yellow oil.

Provenance & Evidence