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US 5,399,725 AGranted
7-oxabicycloheptane carboxylic acid prostaglandin analog intermediates useful in the preparation of anti-thrombotic and anti-vasospastic compounds and method for preparing same
AssigneeBristol-Myers Squibb Company
InventorsMichael A. Poss, Paul D. Pansegrau, Shaopeng Wang, John K. Thottathil, Janak Singh, Richard H. Mueller
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Abstract
A method is provided for preparing carboxylic acid intermediates of the structure ##STR1## wherein an aldehyde of the structure ##STR2## is prepared and subjected to a Horner-Emmons reaction to form the ester of the structure ##STR3## and the ester is hydrogenated to the carboxylic acid which may be used in making the final anti-thrombotic--anti-vasospastic compounds.
Claims4
A method for preparing an alcohol-amide of the structure ##STR52## wherein R.sup.7 is aryl or lower alkyl, R.sup.8 is H, aryl or lower alkyl, and
- R.sup.9 is H, OH or lower alkyl, which comprises providing an imide of the structure ##STR53## reacting the imide with a metallated aryl compound of the structure ##STR54## where Metal is MgBr or Li, to form a hemi-aminol of the structure ##STR55## and reducing the above alcohol to form the alcohol-amide as defined above.
Dependencies are inferred from the claim text.