Synthesis of ethyl-4(3'-methoxyphenyl)-1-methyl piperidine-3-car

Details Synthesis of ethyl-4(3'-methoxyphenyl)-1-methyl piperidine-3-car Synthesis of ethyl-4(3'-methoxyphenyl)-1-methyl piperidine-3-car

1981-03-16

1984-03-06

Coughlan, Jr., Paul M.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

260465D, 546216, 560 55, C07D21176, C07D29514

Patent

active

044355726

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: 2585210 (1952-02-01), Albertson
patent: 3216898 (1965-11-01), Fellows
Koelsch JACS, 65, 2459-2460 (1943).

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