Synthesis of 4A-aryl-decahydroisoquinolines

Details Synthesis of 4A-aryl-decahydroisoquinolines Synthesis of 4A-aryl-decahydroisoquinolines

1978-04-26

1980-02-19

Hollrah, Glennon H.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546192, C07D21126, C07D21724

Patent

active

041895835

ABSTRACT:
This invention relates to a process for the production of 4a-aryldecahydroisoquinolines where the aryl group is selected as 3-methoxy phenyl. These compounds are morphine analogs and show utility similar to the known morphine, codeine, and thebaine. In this process particular novelty is asserted for the production of a nipecotic ester ethyl 4-(3'-methoxyphenyl)-1-methyl piperidine-3-carboxylate. Furthermore, novelty is asserted for the step of conversion of the nipecotates through cyclization to cis- or trans-tert-butyl 1,6-dioxo-4a-(3'-methoxyphenyl)-2-methyldecahydroisoquinoline-7-carboxylat e, which may also be easily converted to the keto amide, trans-1,6-dioxo-4a-(3'-methoxyphenyl)-2-methyldecahydroisoquinoline.

REFERENCES:
patent: 3953434 (1976-04-01), Hauck et al.

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