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Reaktionen von (−)-Ephedrin bzw. (+)-Norpseudoephedrin und Derivaten mit N,N-Dimethylacetamid-dimethylacetal und N,N,-Dimethylformamid-dimethylacetal

Reactions of (−)-ephedrine, (+)-norpseudoephedrine and derivatives with N,N-dimethylacetamid-dimethylacetal and N,N-dimethylformamid-dimethylacetal

  • Organische Chemie Und Biochemie
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Summary

The reactivity of (−)-ephedrine (2) and (+)-norpseudoephedrine (3) towards the amidacetals1 a/b has been studied. Both2 and3 were acetylated resp. formylated at first at the amino group. Nevertheless, derivatives of2 and3 possessing a trisubstituted amino group react with1 a in a [3.3] sigmatopic rearrangement toortho substituted dimethylcarbamoylmethyl derivatives. By subsequent reduction with lithiumaluminiumhydride the aromatic compounds8,13, and18 with two aminoethyl groups are easily available. In contrast to these results1 b did not furnish any rearrangement products.

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Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Universität Wien, A-1090, Wien, Österreich

    M. Köhl, H. Spreitzer & W. Fleischhacker

Authors
  1. M. Köhl
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  2. H. Spreitzer
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  3. W. Fleischhacker
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Köhl, M., Spreitzer, H. & Fleischhacker, W. Reaktionen von (−)-Ephedrin bzw. (+)-Norpseudoephedrin und Derivaten mit N,N-Dimethylacetamid-dimethylacetal und N,N,-Dimethylformamid-dimethylacetal. Monatsh Chem 123, 911–918 (1992). https://doi.org/10.1007/BF00811546

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  • DOI: https://doi.org/10.1007/BF00811546

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