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Mild Reductive Cleavage of α-Aminoethers

URN to cite this document:
urn:nbn:de:bvb:355-epub-156590
DOI to cite this document:
10.5283/epub.15659
Lee, D. U. ; Wiegrebe, Wolfgang
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Date of publication of this fulltext: 06 Jul 2010 08:44


Abstract

l,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinoline (1) is converted by ethyl chloroformate (ECF)/NaBH3CN to 2-[ß-(N-ethoxycarbonyl-N-methyl)aminoethyl]-4,5-dimethoxytoluene (4) via the quaternary urethane 2, The same procedure leads from laudanosine (5) to the dibenzyl derivative 9. The reaction with ECF/NaBH3CN followed by LiAlH4 reduction is a versatile approach to Emde degradation ...

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