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Paper | Regular issue | Vol 26, No. 10, 1987, pp.2703-2710
Published online, 1st January, 1970
DOI: 10.3987/R-1987-10-2703
An Efficient Synthesis of 14-Halogenomethyl-substituted C-Normorphinans

Martin Kratzel and Wilhelm Fleischhacker

*Institute of Pharmaceutical Chemistry, University of Vienna, Währinger Strasse 10, A-1090 Vienna, Austria


Nucleophilic ring-opening reaction of 7,14-cyclo-dihydrocodeinone 1 resulted in a watersoluble quaternary ammonium salt 3. However, similar reaction of 1 under acetalization conditions led to the ring cleavaged 14-halogenomethylacetals 4, 7 and 8 (a-c) in high yields. When the acetals were hydrolyzed, the formation of cyclic ammDnium compounds (3) was unavoidable.