US4102902A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
Assignee: Eli Lilly and Co
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Filing: 1976-11-10
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Granted: 1978-07-25
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Expires: 1996-11-10
Abstract
Abstract An optically active 4-(4-substituted-2,6-dihydroxyphenyl)-6,6-dimethyl-2-norpinanone is reacted with a protonic acid to provide an optical isomer of a cis-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one. Reaction of said norpinanone with a Lewis acid provides an optical isomer of trans-1-hydroxy-3-substituted-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one. The optically active norpinanones are prepared by reaction of a 5-substituted-resorcinol with an optically active 6,6-dimethyl-2,4-diacetoxy-2-norpinene or an optically active 6,6-dimethyl-2,2-diacetoxy-3-norpinene, which compounds are derived from optically active β-pinenes.
Inventors
- 👤 Robert A. Archer
- 👤 William A. Day
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 04:15
CPC Classifications
C; C07; C07C; C07C49/00; C07C49/587; C07C49/703; C07C49/747; C07C45/00; C07C45/51; C07C45/54; C07D; C07D311/00; C07D311/02; C07D311/78; C07D311/80
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
66 words
A process for preparing an optically active 6a,10a-cis compound of the formula ##STR8## wherein: R 4 is C 5 -C 10 alkyl, C 5 -C 10 alkenyl, C 5 -C 8 cycloalkyl and C 5 -C 10 cycloalkenyl; comprising reacting a compound of the formula ##STR9## with a protonic acid selcted from hydrochloric acid, sulfuric acid, phosphoric acid, and para-toluenesulfonic acid in an unreactive organic solvent.
Claim 2
Dependent Claim
66 words
A process for preparing an optically active 6a,10a-cis compound of the formula ##STR8## wherein: R 4 is C 5 -C 10 alkyl, C 5 -C 10 alkenyl, C 5 -C 8 cycloalkyl and C 5 -C 10 cycloalkenyl; comprising reacting a compound of the formula ##STR9## with a protonic acid selcted from hydrochloric acid, sulfuric acid, phosphoric acid, and para-toluenesulfonic acid in an unreactive organic solvent.
Claim 3
Dependent Claim
12 words
The process according to claim 1 wherein the acid is sulfuric acid.
Claim 4
Dependent Claim
17 words
The process according to claim 2 wherein the solvent is a halogenated hydrocarbon or an aromatic solvent.
Claim 5
Dependent Claim
12 words
The process according to claim 3 wherein the acid is para-toluenesulfonic acid.
Claim 6
Dependent Claim
64 words
The process according to claim 4 wherein the compound of the formula ##STR10## wherein: R 4 is C 5 -C 10 alkyl, C 5 -C 10 alkenyl, C 5 -C 8 cycloalkyl or C 5 -C 8 cycloalkenyl is reacted with para-toluenesulfonic acid in chloroform for from about 12 to about 36 hours at a temperature of from about 30° to about 80° C.
Claim 7
Dependent Claim
20 words
The process according to claim 5 wherein optically active 4-[4-(1,1-dimethylheptyl)-2,6-dihydroxyphenyl]-6,6-dimethyl-2-norpinanone is reacted with para-toluenesulfonic acid to provide optically active cis-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]pyran-9-one.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-07-24 | 1982-01-23 | 1982-07-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-07-24 | 1986-01-23 | 1986-07-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-07-24 | 1990-01-23 | 1990-07-25 | $7700.00 | Window Closed / Lapsed |