Synthesis of functionalized adamantanes from fluoroadamantanes

Selective introduction of functional groups on the tert-carbon of adamantane was performed by substitution with fluorides. A methyl, phenacyl, aryl, cyclohexyl, alkoxy, or azido group was introduced into the adamantane skeleton without influencing the other functional groups present. Various functionalized adamantanes were synthesized using this scheme. A fluorinated analog of memantine (3-fluoro-5,7-dimethyl-1-adamantylammonium acetate 25) was synthesized from methyl 3,5-dimethyladamantane-1-carboxylate 6.