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Cleavage of 1-Benzyltetrahydroisoquinolines to Secondary Amines via Urethanes

URN to cite this document:
urn:nbn:de:bvb:355-epub-156301
DOI to cite this document:
10.5283/epub.15630
Kim, W.-J. ; Lee, D.-U. ; Wiegrebe, Wolfgang
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Date of publication of this fulltext: 01 Jul 2010 08:56


Abstract

2,2,2-Trichloroethyl chloroformate and benzyl chloroformate cleave 1-benzyl-1,2,3,4-tetrahydro- 2-methylisoquinolines of type 1 to yield tertiary stilbene urethanes of type 2 which are easily reduced or hydrogenolyzed to secondary amines. 6'-(Hydroxymethyl)-laudanosine (4) is converted by these reagents to the isochroman urethanes 11 and 12 which are split to yield the secondary amine 8 without ...

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