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Degradation of 1-Benzyl-1,2,3,4-tetrahydroisoquinolines (Laudanosine) with Ethyl chloroformate: Gedamer's Intermediate

Angerer, S. von and Eibler, E. and Lee, D.-U. and Wiegrebe, Wolfgang (1989) Degradation of 1-Benzyl-1,2,3,4-tetrahydroisoquinolines (Laudanosine) with Ethyl chloroformate: Gedamer's Intermediate. Scientia Pharmaceutica (Sci. Pharm.) 57, pp. 1-6.

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Abstract

Gadamer has postulated the α-chlorobisbenzyl derivate 2a as an intermediate of the
degradation of laudanosine [(-)-1] to the stilbene 3 by ethyl chloroformate. Optically active 2a is
easily hydrolyzed to the corresponding carbinol 2b. The optical purity of 2b is determined via
diastereomeric esters.

Als Zwischenprodukt des Chlorameisensäureethylester-Abbaus von Laudanosin [(-)-)1] zum
Stilben 3 hat Gadamer das α-Chlorbisbenzylderivat 2a formuliert. Optisch aktives 2a wird leicht
zum entsprechenden Carbinol 2b hydrolysiert, dessen optische Reinheit über diastereomere Ester
bestimmt wird.

Item Type:	Article
Institutions:	Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Wiegrebe
Keywords:	1-Benzyl-1,2,3,4-tetrahydroisoquinolines, Ethyl chloroformate, Mosher-Esters
Subjects:	500 Science > 540 Chemistry & allied sciences
Status:	Published
Refereed:	Yes, this version has been refereed
Created at the University of Regensburg:	Unknown
Owner:	Universitätsbibliothek Regensburg
Deposited On:	08 Jul 2010 06:45
Last Modified:	21 Jul 2011 00:32
Item ID:	15694

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