Preparation of vincadifformine

Details Preparation of vincadifformine Preparation of vincadifformine

1977-12-29

1979-05-15

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

26032614R, 546 85, C07D48716

Patent

active

041549430

ABSTRACT:
The invention relates to the preparation of vincadifformine.
Tetrahydro-.beta.-carboline (II) is reacted with benzoyl chloride to provide 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-[3,4b]-indole (III). Then compound (III) is reduced to give 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4b]-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into chloroindolenine derivative (V) which is immediately treated with thallium t-butyl methyl malonate to give t-butyl methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5-carboxylate (VII). Compound (VII) is hydrogenated to give methyl 1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5-carboxylate (IX). In an alternative embodiment, compound (VI) can be hydrogenated to methyl t-butyl 1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5,5-dicarboxylate (VIII) which is then decarboxylated into compound (IX). Compound (IX) is condensed with 1-bromo-4-formyl-hexane to yield vincadifformine (I).

REFERENCES:
Kutney et al., "Journal of the American Chemical Society", 90:14 (Jul.) 1968.
Laronze et al., "Tetrahedron Letters", No. 6, pp. 491-494 (1974).
Stork et al., J.A.C.S., 85:2872 (1963).
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