7-oxabicycloheptane amino-alcohol intermediates useful in making

Details 7-oxabicycloheptane amino-alcohol intermediates useful in making 7-oxabicycloheptane amino-alcohol intermediates useful in making

1988-01-27

1989-03-28

Rotman, Alan L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549463, C07D30700, C07D26322

Patent

active

048165794

ABSTRACT:
A process is provided for preparing a 7-oxabicycloheptane amino alcohol intermediate of the general structure ##STR1## (wherein the above structure represents (D) of (L) isomers) which is useful in preparing thromboxane A.sub.2 receptor antagonists. This intermediate is prepared by reacting mesoanhydride with an aryl amine ##STR2## wherein R is alkyl, CH.sub.2 OH, CO.sub.2 H or CO.sub.2 alkyl, to form the acid ##STR3## which is reduced by treatment with lithium aluminum hydride or diisobutylaluminum hydride or Red-Al to form the alcohol ##STR4## wherein R.sup.1 is CH.sub.2 OH when R is CO.sub.2 H, CO.sub.2 alkyl or CH.sub.2 OH, and R.sup.1 is alkyl; where in the above alcohol R.sup.1 is CH.sub.2 OH, such alcohol compound is treated with an alkyl chloroformate in the presence of base such as an alkali metal alkoxide to form the alcohol ##STR5## which undergoes cleavage by treatment with alkali metal, ammonia and acid to form the amino alcohol intermediate.

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