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

✍ Scribed by Roland Heckendorn

• Publisher: John Wiley and Sons
• Year: 1987
• Tongue: German
• Weight: 532 KB
• Volume: 70
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19870700730

✦ Synopsis

The stereoselectivity of the reduction of 5-carbamoyl-l0, I 1-dihydro-1 l-oxo-SH-dibenz[bflazepine-lO-yl acetate (6), prepared in two steps from 10, I l-dihydro-lO-oxo-5H-dibenz[hflazepine-5-carboxamide (4), has been studied. Among the reagents used, diisobutylaluminum hydride (DIBAH) was found to give the highest trans/& dial ratio. This allowed the preparation of the important trans-dial metabolite 3 of carbamazepine (1).