C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/361.1, 260/3
C07D 493/08 (2006.01)
Patent
CA 1305713
HA399 Abstract PROCESS FOR PREPARING 7-OXABICYCLOHEPTANE AMINO-ALCOHOL INTERMEDIATES USEFUL IN MAKING THROMBOXANE A2 RECEPTOR ANTAGONISTS AND NOVEL INTERMEDIATES PRODUCED THEREIN A process is provided for preparing a 7-oxabicycloheptane amino alcohol intermediate of the general structure Image or HA399 Image (wherein the above structures represents (D) or (L) isomers) which is useful in preparing thromboxane A2 receptor antagonists. This intermediate is prepared by reacting mesoanhydride with an aryl amine Image wherein R is alkyl, CH2OH, CO2H or CO2alkyl, to form the acid Image HA399 which is reduced by treatment with lithium aluminum hydride or diisobutylaluminum hydride or Red-Al to form the alcohol Image wherein R1 is CH2OH when R is CO2H, CO2alkyl or CH2OH, and R1 is alkyl when R is alkyl; where in the above alcohol R1 is CH2OH, such alcohol compound is treated with an alkyl chloroformate in the presence of base such as an alkali metal alkoxide to form the alcohol Image which undergoes cleavage by treatment with alkali metal, ammonia and acid to form the amino alcohol intermediate. Where in the above alcohol R1 is alkyl, that is HA399 Image such alcohol may be hydrogenated to form the aminoalcohol intermediate. All of the above 7-oxabicycloheptane compounds are novel and also form part of the present invention.
536604
E.r. Squibb & Sons Inc.
Osler Hoskin & Harcourt Llp
LandOfFree
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