Process for the synthesis of vincadifformine and relatd...

Details Process for the synthesis of vincadifformine and relatd... Process for the synthesis of vincadifformine and relatd...

C - Chemistry, Metallurgy

07

D

260/299, 260/241

C07D 471/14 (2006.01) C07C 43/313 (2006.01) C07C 43/315 (2006.01) C07C 45/41 (2006.01) C07C 45/51 (2006.01) C07C 47/14 (2006.01) C07C 309/66 (2006.01) C07C 391/02 (2006.01) C07D 301/14 (2006.01) C07D 303/32 (2006.01) C07D 303/40 (2006.01) C07D 309/30 (2006.01) C07D 471/04 (2006.01) C07D 471/20 (2006.01) C07D 487/00 (2006.01) C07D 487/04 (2006.01) C07D 487/20 (2006.01)

Patent

CA 1142178

ABSTRACT OF THE DISCLOSURE -------------------------- This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of vincamine and other related compounds possessing interesting psycho- pharmacologic properties A N-benzyl-tetrahydro-?-carboline compound (III) is halogenated with t-butyl hypochlorite to obtain a haloindolenine compound which is directly treated with a metal dialkyl malonate such as thallium dialkyl malonate to provide a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5,5-dicarboxylate compound, said latter compound being hydrogenated to provide a dialkyl 1,2,3,4,5,6- hexahydroazepino (4,5-b) indole-5,5-dicarboxylate, said latter compound being condensed with a functionalised aldehyde, typically a haloaldehyde, to provide vincadifformine or a related derivative by passing through an intermediate compound being a salt of a dialkyl 3,3-(alkenyl)-1,2,3,4,5,6- hexahydroazepino (4,5-b) indolinium-(5,5)-dicarboxylate.

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