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US4150236A
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Steroidal intermediates from the condensation product of dimethyl-3-ketoglutarate and glyoxal
Assignee: United States Department of Health and Human Services
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Filing: 1977-07-19
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Granted: 1979-04-17
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Expires: 1997-07-19
Abstract
Abstract Tricyclic aromatic compounds of the formula ##STR1## including those wherein: (A) R 1 is H, R 2 is carbomethoxy, and R 3 is methyl; (b) R 1 is acetyl, R 2 is carbomethoxy, and R 3 is methyl; (c) R 1 and R 3 are methyl and R 2 is carbomethoxy; (d) R 1 , R 2 , and R 3 are hydrogen; and (e) R 1 and R 3 are methyl and R 2 is hydrogen Are intermediates for the total synthesis of steroids.
Inventors
- 👤 Ulrich Weiss
- 👤 Kenner C. Rice
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 15:41
CPC Classifications
C; C07; C07C; C07C62/00; C07C62/30; C07C62/38
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
163 words
A method for the synthesis of a tricyclic aromatic compound of the formula ##STR18## wherein R 1 is hydrogen, R 2 is carbomethoxy, and R 3 is methyl comprising the steps of: (a) condensing three moles of a dimethyl 3-ketoglutarate of the formula R 3 OOCCH 2 COCH 2 COOR 3 with two moles of glyoxal to produce a hexacarbomethoxy compound of the formula ##STR19## wherein R 3 is methyl; (b) hydrolyzing the hexacarbomethoxy compound to a dicarbomethoxyaldol of the formula ##STR20## (c) acetylating the dicarbomethoxyaldol to an acetoxy compound of the formula ##STR21## wherein Ac is acetoxy; (d) thermolyzing the acetoxy compound to a tricyclic compound of the formula ##STR22## which spontaneously aldolizes to an intramolecular aldol of the formula ##STR23## and treating the intramolecular aldol with alkali metal methoxide to form the tricyclic aromatic compound of the formula ##STR24## wherein R 3 is as above; or treating said acetoxy compound with the alkali metal methoxide to form said tricyclic aromatic compound.
Claim 2
Independent Claim
163 words
A method for the synthesis of a tricyclic aromatic compound of the formula ##STR18## wherein R 1 is hydrogen, R 2 is carbomethoxy, and R 3 is methyl comprising the steps of: (a) condensing three moles of a dimethyl 3-ketoglutarate of the formula R 3 OOCCH 2 COCH 2 COOR 3 with two moles of glyoxal to produce a hexacarbomethoxy compound of the formula ##STR19## wherein R 3 is methyl; (b) hydrolyzing the hexacarbomethoxy compound to a dicarbomethoxyaldol of the formula ##STR20## (c) acetylating the dicarbomethoxyaldol to an acetoxy compound of the formula ##STR21## wherein Ac is acetoxy; (d) thermolyzing the acetoxy compound to a tricyclic compound of the formula ##STR22## which spontaneously aldolizes to an intramolecular aldol of the formula ##STR23## and treating the intramolecular aldol with alkali metal methoxide to form the tricyclic aromatic compound of the formula ##STR24## wherein R 3 is as above; or treating said acetoxy compound with the alkali metal methoxide to form said tricyclic aromatic compound.
Claim 3
Dependent Claim
31 words
The method of claim 1, including the further step of etherifying the hydroxy of said tricyclic aromatic compound to a dimethoxy compound of the formula ##STR25## wherein R 1 is methyl.
Claim 4
Dependent Claim
31 words
The method of claim 1 including the further step of esterifying the hydroxy of said tricyclic aromatic compound to a diacetoxy compound of the formula ##STR26## wherein R 1 is acetyl.
Claim 5
Dependent Claim
31 words
The method of claim 1 including the further steps of hydrolyzing said tricyclic aromatic hydrocarbon to a diacid of the formula ##STR27## and decarboxylating to an acid of the formula ##STR28##
Claim 6
Dependent Claim
25 words
The method of claim 4 including the further step of etherifying the acid to a dimethoxyacid of the formula ##STR29## wherein R 1 is methyl.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-04-16 | 1982-10-16 | 1983-04-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-04-16 | 1986-10-16 | 1987-04-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-04-16 | 1990-10-16 | 1991-04-17 | $7700.00 | Window Closed / Lapsed |