US3932467A
Expired / Lapsed
US
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Process for the production of 2β-formyl 3α-protected hydroxy-5-oxocyclopentane-1α-heptanoic acids and esters corresponding
Assignee: GD Searle LLC
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Filing: 1973-08-28
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Granted: 1976-01-13
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Expires: 1993-08-28
Abstract
Abstract 2-Formyl-3-protected hydroxy-5-oxocyclopent-1-eneheptanoic acid and its esters are stereoselectively reduced to the corresponding 2β-formyl-3α-protected hydroxy-5-oxocyclopentane-1α-heptanoic acid and esters with chromous sulfate. The compounds so produced are useful as intermediates to PGE 1 and its esters, which compounds exhibit hypotensive and smooth muscle-stimulating properties.
Inventors
- 👤 Masateru Miyano
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 07:01
CPC Classifications
C; C07; C07D; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; C07C; C07C405/00; C07C59/00; C07C59/185; C07C59/225; C07C59/40; C07C59/76; C07C59/90; C07C59/92; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/54; C07F9/5407
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
45 words
A compound of the formula ##SPC3## wherein R 1 is hydrogen or a lower alkyl, tetrahydropyran-2-yl,4-(lower alkoxy)tetrahydropyran-4-yl or tri(lower alkyl)silyl radical, R 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.
Claim 2
Dependent Claim
45 words
A compound of the formula ##SPC3## wherein R 1 is hydrogen or a lower alkyl, tetrahydropyran-2-yl,4-(lower alkoxy)tetrahydropyran-4-yl or tri(lower alkyl)silyl radical, R 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.
Claim 3
Dependent Claim
98 words
A process for the production of a compound of the formula ##SPC4## wherein R 1 is hydrogen, a lower alkyl, tetrahydropyran-2-yl, 4-(lower alkoxy)tetrahydropyran-4-yl or tri(lower alkyl)silyl radical and R 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 1 and R 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
Claim 4
Dependent Claim
98 words
A process for the production of a compound of the formula ##SPC4## wherein R 1 is hydrogen, a lower alkyl, tetrahydropyran-2-yl, 4-(lower alkoxy)tetrahydropyran-4-yl or tri(lower alkyl)silyl radical and R 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 1 and R 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
Claim 5
Dependent Claim
21 words
A process as in claim 1, wherein the compound of formula II is racemic and the reducing agent is chromous sulfate.
Claim 6
Dependent Claim
37 words
A process as in claim 1 which comprises contacting a racemic compound of the formula ##SPC6## wherein R 1 is hydrogen or a lower alkyl tetrahydropyran-2-yl radical and R 2 is a tetrahydropyran-2-yl radical, with chromous sulfate.
Claim 7
Dependent Claim
18 words
A process as in claim 1 which comprises contacting dl-2-formyl-3-(tetrahydropyran-2-yl)oxy-5-oxocyclopent-1-eneheptanoic acid with chromous sulfate, thereby forming dl-2β-formyl-3α-(tetrahydropyran-2-yl)-oxy-5-oxocyclopentane-1.alpha.-heptanoic acid.
References Cited (Backward Citations)
US3532721A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-12 | 1979-07-14 | 1980-01-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-12 | 1983-07-14 | 1984-01-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-12 | 1987-07-14 | 1988-01-13 | $7700.00 | Window Closed / Lapsed |