48141-64-6Relevant articles and documents
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Dehmlow,E.V. et al.
, p. 363 - 366 (1977)
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The Reductive Cleavage of Cyclic Aminol Ethers to N,N-Dialkylamino-derivatives: Modifications to the Eschweiler-Clarke Procedure
Page, Philip C. Bulman,Heaney, Harry,Rassias, Gerasimos A.,Reignier, Serge,Sampler, Edward P.,Talib, Salem
, p. 104 - 106 (2007/10/03)
The reductive cleavage of cyclic aminol ethers to give N-alkylamino-derivatives in very high yields can be achieved using chlorotrimethylsilane in the presence of sodium cyanoborohydride: in the case of cyclic aminol ethers derived from formaldehyde the Eschweiler-Clarke reaction can be carried out in formic acid heated under reflux in the absence of formaldehyde.
Reactions of (-)-Ephedrine, (+)-Norpseudoephedrine and Derivatives with N,N-Dimethylacetamid-dimethylacetal and N,N-Dimethylformamid-dimethylacetal
Koehl, M,Spreitzer, H.,Fleischhacker, W.
, p. 911 - 918 (2007/10/02)
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 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.