Cilobamine
Introduction '''Cilobamine''' is a drug which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI) and has stimulant and antidepressant effects.It can clearly be seen that the structure is based on dichloroisoprenaline that has been fused onto the bicycloalkane scaffold.
Synthesis Patent:An intramolecular Dieckmann cyclization on methyl 4-(2-methoxy-2-oxoethyl)cyclohexanecarboxylate 1401222-79-4 ('''3''') with sodium hydride base gives reaction Methyl 3-oxobicyclo2.2.2octane-2-carboxylate 30144-30-0 ('''4'''). Treatment with sodium nitrite introduces an isonitroso group adjacent to the ketone, giving 3-Hydroxyiminobicyclo2.2.2octan-2-one,  CID:131066320 ('''5'''). Addition of the aryl Grignard reagent, and reduction of the oxime gives  CID:154108204 ('''6'''). A reductive amination of the primary amino group with acetone then completed the synthesis of cilobamine ('''7''').
See also * Fencamfamine* Manifaxine
References