Enantiomerically selective synthesis of certain N-substituted-2-

Details Enantiomerically selective synthesis of certain N-substituted-2- Enantiomerically selective synthesis of certain N-substituted-2-

1989-04-17

1990-09-18

Lee, Mary

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30700

Patent

active

049580361

ABSTRACT:
A process is provided for preparing a 7-oxabicycloheptane amino alcohol intermediate of the general structure ##STR1## (wherein the above structures represents (D) or (L) isomers)
which is useful in preparing thromboxane A.sub.2 receptor antagonists. This intermediate is prepared by reacting mesanhydride 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 when R 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.
Where in the above alcohol R.sup.1 is alkyl, that is ##STR6## 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.

REFERENCES:
patent: 4143054 (1979-03-01), Sprague
patent: 4187236 (1980-02-01), Sprague
patent: 4220594 (1980-09-01), Sprague
patent: 4228180 (1980-10-01), Sprague
patent: 4254044 (1981-03-01), Sprague
patent: 4416896 (1983-11-01), Nakane et al.
patent: 4456615 (1984-06-01), Nakane et al.
patent: 4456617 (1984-06-01), Nakane et al.
patent: 4663336 (1987-05-01), Nakane et al.
B. S. Joshi et al., "Synthesis & Anticonvulsant Activity of 7-Oxabicyclo[2.2.1]Heptane Derivatives: Part II-N-Alkyl, N-Aryl & N-Heteroaryl Derivatives of 3,6-Epoxyhexahydrophthalic Acid Amides," Indian Journal of Chemistry, vol. 22B, Feb. 1983, pp. 136-139.
Sprague et al., J. Med. Chem., 28, pp. 1580-1590 (1985).

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