Process for epimerization at C.sub.6 of 3,4,5,6-tetrahydro-2H-py

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549214, 556419, 556420, C07D30910

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active

045888205

ABSTRACT:
An external bond at the 6-position of a 3,4,5,6-tetrahydro-2H-pyran-2-one, as found in the 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors, is readily epimerized by treating an amide of the corresponding hydroxy acid with a sulfonyl chloride reagent.

REFERENCES:
patent: 4198425 (1980-04-01), Mistui et al.
patent: 4444784 (1984-04-01), Hoffman et al.
March, Jerry, Advanced Organic Chemistry: Reactions, Mechanisms & Structure, McGraw-Hill, N.Y. (1968) pp. 268-269, 372-375.
Eliel, Ernest, Stereo Chemistry of Carbon Compounds, (1962) McGraw-Hill Book Co., N.Y., pp. 116-119, 38-39.
Johnson et al, Nucleophilic Displacement on Sulfur, The Inversion of Sulfoxide Configurations, Journal Amer. Chem. Society, vol. 87, No. 23, pp. 5404-5409 (1965).

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