Ethanol → HCID 12151259, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.52 g (10 mmole) of 3-oxo-tricyclo[2.2.1.02,6]heptane-1-carboxylic acid, 0.78 g (12 mmole) of potassium cyanide and 3.36 g (35 mmole) of ammonium carbonate in 75 mL of ethanol-water (1:1) was stirred at 75° C. for 18 hours. An additional 2-4 mmole of potassium cyanide and 6-12 mmole of ammonium carbonate were added and stirring at 75° C. was continued for 18 hours. The ethanol was then allowed to evaporate and the reaction mixture adjusted to pH 1 with concentrated HCl. Upon cooling the mixture to 0° C., a white precipitate formed and was removed by filtration and washed with ice-cold water and ethyl acetate and dried in vacuum to give 1.32 g of the title compound. Concentration of the mother liquor led to the isolation of an additional 0.22 g of white solid. Thus, 1.54 g of the title compound were obtained as a mixture of diastereomers.

Provenance & Evidence