Synthesis of trans-10,11-Dihydro-10,11-dihydroxy-5H-dibenz[b,f]azepine-5-carboxamide, a Major Metabolite of Carbamazepine

The stereoselectivity of the reduction of 5‐carbamoyl‐10,11‐dihydro‐11‐oxo‐5H‐dibenz[b,f]azepine‐10‐yl acetate (6), prepared in two steps from 10,11‐dihydro‐10‐oxo‐5H‐dibenz[b,f]azepine‐5‐carboxamide (4), has been studied. Among the reagents used, diisobutylaluminum hydride (DIBAH) was found to give...

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Veröffentlicht in:	Helvetica chimica acta 1987-11, Vol.70 (7), p.1955-1962
1. Verfasser:	Heckendorn, Roland
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties
Online-Zugang:	Volltext
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Zusammenfassung:	The stereoselectivity of the reduction of 5‐carbamoyl‐10,11‐dihydro‐11‐oxo‐5H‐dibenz[b,f]azepine‐10‐yl acetate (6), prepared in two steps from 10,11‐dihydro‐10‐oxo‐5H‐dibenz[b,f]azepine‐5‐carboxamide (4), has been studied. Among the reagents used, diisobutylaluminum hydride (DIBAH) was found to give the highest trans/cis diol ratio. This allowed the preparation of the important trans‐diol metabolite 3 of carbamazepine (1).
ISSN:	0018-019X 1522-2675
DOI:	10.1002/hlca.19870700730