Hexacyclonate

Hexacyclonate is a stimulant drug. It has been used for the treatment of alcoholism and for increasing motivation in elderly patients, but Gevilon is now mainly used for the treatment of hyperlipoproteinaemia. It is chemically similar to the anticonvulsant gabapentin, with a hydroxyl group replacing the amine.
The latter use may be incorrectly assigned, as "Gevilon" has been used as a trade name for gemfibrozil, a well-known drug for dislipidemia.

Synthesis

The treatment of 1,1-Cyclohexanediacetic acid with acetic anhydride led to Cyclohexanediacetic anhydride . Esterification with methanol led to 1,1-Cyclohexanediacetic acid mono methyl ester . Treatment of the monoacid with potassium hydroxide gave the alkoxide. Treatment with bromine in the presence of tetrachloromethane gave Methyl 3,3-pentamethylene-4-bromobutyrate. Reaction with aqueous lye gave 2-Oxaspirodecan-3-one . Further treatment with aqueous lye completed the synthesis of hexacyclonate.