The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
May. 15, 1979
Filed:
Dec. 29, 1977
Martin E Kuehne, Burlington, VT (US);
University of Vermont, Burlington, VT (US);
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).