Monatshefte fur Chemie p. 911 - 918 (1992)
Update date:2022-08-02
Topics:
Koehl, M
Spreitzer, H.
Fleischhacker, W.
The reactivity of (-)-ephedrine (2) and (+)-norpseudoephedrine (3) towards the amid-acetals 1 a/b has been studied.Both 2 and 3 were acetylated resp. formylated at first at the amino group.Nevertheless, derivatives of 2 and 3 possessing a trisubstituted amino group react with 1 a in a <3.3> sigmatropic rearrangement to ortho substituted dimethylcarbamoylmethyl derivatives.By subsequent reduction with lithiumaluminiumhydride the aromatic compounds 8, 13, and 18 with two aminoethyl groups are easily available.In contrast to these results 1 b did not furnish any rearrangement products. Keywords. (-)-Ephedrine; (+)-Norpseudoephedrine; N,N-Dimethylacetamid-dimethylacetal; N,N-Dimethylformamid-dimethylacetal; Sympathomimetic effects; Sigmatropic rearrangements.
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(1992)