2,5-Dimethylcyclopentan-1-one → 6,9-Dimethyl-5,6,7,8,9,10-hexahydro-6,9-methanobenzocycloocten-11-one

Participants

Reaction Steps

A process for the preparation of the compounds of the present invention which are substituted by alkyl substituents, e.g., methyl substituents in the 6 and/or 9 positions, begins with the treatment of an α,α-dihaloxylene with an alkylated or dialkylated derivative of the appropriate cycloalkanone-enamine. Thus, for example, α,α-dibromoxylene is treated with the pyrrolidine enamine of 2,5-dimethylcyclopentanone to produce the corresponding 6,9-dimethyl-5,6,7,8,9,10-hexahydro-6,9-methanobenzocyclooctene-11-one, followed by thallation as described hereinabove, to introduce the corresponding 2'-hydroxy compound and subsequent conversion to the oxime, followed by catalytic reduction to the desired D,L-11-endo-amino-6,9-dimethyl-5,6,7,8,9,10-hexahydro-6,9-methanobenzocyclooctene.

Provenance & Evidence