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Details for Patent: 4,309,544

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Details for Patent: 4,309,544

Title: Preparation of 6-oxa-1-azatricyclo(6.2.2.0.sup.2,7)dodecane-5-ones
Abstract:The invention relates to the production of compounds of the general formula: ##STR1## wherein X is selected from the group consisting of oxygen, CH.sub.2 and CH radicals, and when X designates oxygen, R designates alkyl, isoalkyl, aralkyl, and substituted aralkyl groups and when X designates CH.sub.2 then R designates alkyl, phenyl or substituted phenyl group, and A-B is a single bond, and when X designates CH.sub.2, R designates alkyl, phenyl or substituted phenyl groups and A-B is a double bond; and physiologically acceptable salts of these, and pharmaceutical composition containing the same as active ingredient.
Inventor(s): Cohen; Sasson (Tel-Aviv, IL), Fisher; Abraham (Holon, IL)
Assignee: The Purdue Frederick Company (Norwalk, CT)
Filing Date:Jul 20, 1979
Application Number:06/058,968
Claims:1. A process for the production of a compound of the formula: ##STR8## wherein R is selected from the group consisting of lower alkyl, cyclopentyl and cyclohexyl, which comprises condensing 2-methylene 3-quinuclidinone with a lower alkyl-substituted R-acetoacetate wherein R has the same definition as above in the presence of sodium alkoxide, and treating the thus obtained intermediate with a mineral acid and water to yield the corresponding 1,4-ethano-6-oxo-7- R-1,2,3,4,6,7,8,8a-octahydroquinoline, which latter is is reduced with hydrogen in the presence of catalytic quantities of palladium on carbon to yield the desired product.

2. A process for the production of a compound of the formula: ##STR9## wherein R is selected from the group consisting of thienyl, phenyl, methylphenyl, methoxyphenyl, chlorophenyl, trifluoromethylphenyl, aminophenyl, di-loweralkylaminophenyl and benzyl, which comprises reacting 2-methylene-3-quinuclidinone with a compound of the formula CH.sub.3 --CO--CH.sub.2 -- R wherein R has the same definition as above in the presence of sodium alkoxide to yield the corresponding o,4-ethano-6-oxo-7- R -1,2,3,4,6,7,8,8a-octahydroquinoline which latter is reduced with hydrogen in the presence of a catalytic quantity of palladium on carbon to yield the desired product.
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