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US 3,932,467 AGranted
Process for the production of 2.beta.-formyl 3.alpha.-protected hydroxy-5-oxocyclopentane-1.alpha.-heptanoic acids and esters corresponding
AssigneeG. D. Searle & Co.
InventorMasateru Miyano
Life of this patent
Estimating the term…
Abstract
2-Formyl-3-protected hydroxy-5-oxocyclopent-1-eneheptanoic acid and its esters are stereoselectively reduced to the corresponding 2.beta.-formyl-3.alpha.-protected hydroxy-5-oxocyclopentane-1.alpha.-heptanoic acid and esters with chromous sulfate. The compounds so produced are useful as intermediates to PGE.sub.1 and its esters, which compounds exhibit hypotensive and smooth muscle-stimulating properties.
Claims5
A compound of the formula ##SPC3##
- wherein R.sub.1 is hydrogen or a lower alkyl, tetrahydropyran-2-yl,4-(lower alkoxy)tetrahydropyran-4-yl or tri(lower alkyl)silyl radical, R.sub.2 is a tetrahydropryan-2-yl,4-(lower alkoxy)tetrahydropryan-4-yl or tri(lower alkyl)silyl radical and the wavy line represents the racemic mixture or the optically active 3(R) isomer.
A process for the production of a compound of the formula ##SPC4##
- wherein R.sub.1 is hydrogen, a lower alkyl, tetrahydropyran-2-yl, 4-(lower alkoxy)tetrahydropyran-4-yl or tri(lower alkyl)silyl radical and R.sub.2 is a tetrahydropyran-2-yl, 4-(lower alkoxy)tetrahydropyran-4-yl or tri(lower alkyl)silyl radical which comprises contacting a compound of the formula ##SPC5##
- wherein R.sub.1 and R.sub.2 are defined as above and the wavy line represents the racemic (RS) compound or the optically active R isomer, with chromous sulfate, chromous acetate or chromous perchlorate reducing agent, wherein the molar ratio of reducing agent to compound of formula II is about 2:1
Dependencies are inferred from the claim text.