Water → HCID 659308, compound

Participants

Reaction Steps

N,N′-Di-cyclohexyl L-tartaramide was prepared by the reaction of cyclohexyl amine with diethyl L-tartrate. Diethyl L-tartrate (19.997 g, 1.0 eq) and HPLC grade methanol (40 mL) were weighed into a 250 mL round-bottomed flask equipped with a teflon coated magnetic stir bar. Cyclohexyl amine (20.205 g, 2.0 eq) was slowly poured into the stirring diethyl L-tartrate solution. Some fuming and a color change from water-white to pale yellow were observed. Additional methanol (10 mL) was used to rinse all of the amine into the reaction flask. After stirring the solution for 30 min, the flask was stoppered and refrigerated at approximately 45° F. (70C). The product crystallized after 3 days at 45° F. (7° C.). The white crystals were filtered, washed with methanol (2×15 mL), and dried under vacuum. A first crop of 3.952 g (12.65 mmole, 13% yield) were obtained in this manner, and a second crop of 16.063 g were obtained by removing the solvent under vacuum. Overall yield was 66%.

Provenance & Evidence