Ulrich Beutler

New synthesis of oxcarbazepine via remote metalation of protected N-o-tolyl-anthranilamide derivatives

Abstract Benzyl and allyl protected N-o-tolyl-anthranilamides were efficiently prepared by Buchwald–Hartwig C–N cross coupling reactions, followed by protection of the amino group. Under directed remote metalation conditions, protected dibenzoazepinones were obtained in good yields. Deprotection of the amine and conversion to an urea furnished a new and efficient synthesis of the antiepileptic drug Trileptal®.

Heterogeneous vs. homogeneous catalysis in manufacturing of terbinafine a case study for route selection of an industrial process

Abstract The antimycotic agent terbinafine can be prepared from the vinylchloride 1 and tert.-butyl-acetylene 2 using different homogeneous or heterogeneous palladium-catalysts. Alternatively terbinafine was synthesized from the allyl acetate 3 and N-methyl-N-(α-methylnaphtyl)-amine 4 with the aid of a polystyrene-supported Pd(PPh 3 ) 4 -catalyst. All processes gave terbinafine in high yield and stereoselectivity. For the selection of a new production process of terbinafine ecological, economical, and technical aspects are compared.