Syntheses in the Isocamphane Series, XXVI. The Synthesis of an Isocamphane-analogous Ephedrine

Article abstract of DOI:10.1007/BF00811254

The synthesis of two new bicyclic phenylethylamine derivatives with potentially simpathomimetic effects is described.The synthesis of the isocamphane analogous apoephedrine (4) starts from the bicyclic methylketone 5 and leads via its α-bromoderivative 6 and the corresponding tosylamidoketone 8 to 4.The synthesis of the title compound 2 has been accomplished by preparing the α-oximinoketone 19 from the bicyclic ethylketone 15 with subsequent reduction to the amino alcohol derivative 20 and final selective monomethylation by the Johnstone procedure via the corresponding trifluoroacetamide. - Keywords: Apoephedrine analogue; Bicyclo<2.2.1>heptyl-N-methylaminoethanol derivative; Bicyclo<2.2.1>heptyl-N-methylaminopropane derivative; C-N-Bond formation; Ephedrine analogue; Isocamphane analoguous drugs; α-Oximinoketone; Simpathomimetica