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Communication | Special issue | Vol 5, No. 1, 1976, pp.85-90
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0085
■ Preferential Removal of a Methylenedioxy Group from Optically Active Isoquinolines

Sidney Teiterl* and Jay P. O’Brien

*The Department of Chemistry Research, Hoffman-La Roghe Inc., Nutley, New Jersey 07110, U.S.A.

Abstract

The optically active dimethoxymethylenedioxy-substituted benzylisoquinoline (2a) and tetrahydroprotoberberine (3a) were O-demethylenated with boron trichloride followed by hydrogenolysis of the bistetrazoyl ether intermediate over Pd-C to afford, with retention of absolute configuration, (2d) and (3d), respctively. In contrast, hydrogenolysis of the dextrorotatory bistetrazoyl aporphine (4c) -a substrate that can readily dehydrogenate-gave the racemate of (4d).