Reaktionen von (?)-Ephedrin bzw. (+)-Norpseudoephedrin und Derivaten mit N,N-Dimethylacetamid-dimethylacetal und N,N,-Dimethylformamid-dimethylacetal |
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Authors: | M Köhl H Spreitzer W Fleischhacker |
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Institution: | (1) Institut für Pharmazeutische Chemie, Universität Wien, A-1090 Wien, Österreich |
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Abstract: | 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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Keywords: | (– )-Ephedrine (+)-Norpseudoephedrine N N-Dimethylacetamid-dimethylacetal N N-Dimethylformamid-dimethylacetal Sympathomimetic effects Sigmatropic rearrangements |
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