US3975440A
Expired / Lapsed
US
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Asymmetric synthesis of organic compounds
Assignee: Hoffmann La Roche Inc
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Filing: 1970-12-09
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Granted: 1976-08-17
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Expires: 1990-12-09
Abstract
Abstract Optically active organic compounds are prepared starting from optically inactive reactants by means of an optically active agent which influences the course of the reaction. In particular optically active compounds having a "meso" type carbon atom undergo an intramolecular ring closure in the presence of an optically active agent to yield an optically active product having one additional ring. The present process is particularly useful in the preparation of optically active bicyclic diketones which are important intermediates in the total synthesis of steroids.
Inventors
- 👤 Zoltan George Hajos
- 👤 David Richard Parrish
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 07:10
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/52; C07C; C07C45/00; C07C45/56; C07C45/61; C07C45/65; C07C45/66; C07C45/67; C07C45/68; C07C45/69; C07C45/72; C07C45/73; C07C49/00; C07C49/385; C07C49/487; C07C49/507; C07C49/513; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/06; C07C2603/10; C07C2603/12; C07C2603/16
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
153 words
A process for the preparation of a compound of the formula ##EQU1## wherein R 1 is lower alkyl, aryl, aralkyl, acylamino, lower alkenyl, lower alkynyl, halogen, lower alkanoyloxy, or lower alkoxy carbonyl; R 2 is hydrogen, lower alkyl, aryl, aralkyl and -(CH 2 ) p R 3 where p is an integer between 0 and 2 inclusive and R 3 is halogen, hydroxy, lower alkoxy, mesyloxy, tosyloxy, cyano or ##EQU2## where R 4 is hydrogen, hydroxy, lower alkyl, lower alkoxy, aryloxy and aryl lower alkoxy and R 5 is oxo, lower alkylenedioxy or arylenedioxy provided, however, that when R 4 is other than hydrogen or lower alkyl, R 5 is oxo; n is an integer between 1 and 5 inclusive; which process comprises reacting a compound of the formula ##SPC14## wherein R 1 and n are as above with a compound of the formula ##EQU3## wherein R 2 is as above in water.
Claim 2
Dependent Claim
153 words
A process for the preparation of a compound of the formula ##EQU1## wherein R 1 is lower alkyl, aryl, aralkyl, acylamino, lower alkenyl, lower alkynyl, halogen, lower alkanoyloxy, or lower alkoxy carbonyl; R 2 is hydrogen, lower alkyl, aryl, aralkyl and -(CH 2 ) p R 3 where p is an integer between 0 and 2 inclusive and R 3 is halogen, hydroxy, lower alkoxy, mesyloxy, tosyloxy, cyano or ##EQU2## where R 4 is hydrogen, hydroxy, lower alkyl, lower alkoxy, aryloxy and aryl lower alkoxy and R 5 is oxo, lower alkylenedioxy or arylenedioxy provided, however, that when R 4 is other than hydrogen or lower alkyl, R 5 is oxo; n is an integer between 1 and 5 inclusive; which process comprises reacting a compound of the formula ##SPC14## wherein R 1 and n are as above with a compound of the formula ##EQU3## wherein R 2 is as above in water.
Claim 3
Dependent Claim
159 words
A process for the preparation of a compound of the formula ##STR8## wherein R 1 is lower alkyl, aryl, aralkyl, acylamino, lower alkenyl, lower alkynyl, halogen, lower alkanoyloxy, or lower alkoxy carbonyl; R 2 is hydrogen, lower alkyl, aryl, aralkyl and--(CH 2 ) p R 3 where p is an integer between 0 and 2 inclusive and R 3 is halogen, hydroxy, lower alkoxy, mesyloxy, tosyloxy, cyano or ##STR9## where R 4 is hydrogen, hydroxy, lower alkyl, lower alkoxy, aryloxy and aryl lower alkoxy and R 5 is oxo, lower alkylenedioxy or arylenedioxy provided, however, that when R 4 is other than hydrogen or lower alkyl, R 5 is oxo; n is an integer between 1 and 5 inclusive; which process comprises reacting a compound of the formula ##SPC15## wherein R 1 and n are as above with a compound of the formula ##STR10## wherein R 2 is as above in a neutral or slightly acidic aqueous solvent medium.
Claim 4
Dependent Claim
159 words
A process for the preparation of a compound of the formula ##STR8## wherein R 1 is lower alkyl, aryl, aralkyl, acylamino, lower alkenyl, lower alkynyl, halogen, lower alkanoyloxy, or lower alkoxy carbonyl; R 2 is hydrogen, lower alkyl, aryl, aralkyl and--(CH 2 ) p R 3 where p is an integer between 0 and 2 inclusive and R 3 is halogen, hydroxy, lower alkoxy, mesyloxy, tosyloxy, cyano or ##STR9## where R 4 is hydrogen, hydroxy, lower alkyl, lower alkoxy, aryloxy and aryl lower alkoxy and R 5 is oxo, lower alkylenedioxy or arylenedioxy provided, however, that when R 4 is other than hydrogen or lower alkyl, R 5 is oxo; n is an integer between 1 and 5 inclusive; which process comprises reacting a compound of the formula ##SPC15## wherein R 1 and n are as above with a compound of the formula ##STR10## wherein R 2 is as above in a neutral or slightly acidic aqueous solvent medium.
Claim 5
Dependent Claim
167 words
A process for the preparation of a compound of the formula ##STR11## wherein R 1 is lower alkyl, aryl, aralkyl, acylamino, lower alkenyl, lower alkynyl, halogen, lower alkanoyloxy, or lower alkoxy carbonyl; R 2 is hydrogen, lower alkyl, aryl, aralkyl and -(CH 2 ) p R 3 where p is an integer between 0 and 2 inclusive and R 3 is halogen, hydroxy, lower alkoxy, mesyloxy, tosyloxy, cyano or ##STR12## where R 4 is hydrogen, hydroxy, lower alkyl, lower alkoxy, aryloxy and aryl lower alkoxy and R 5 is oxo, lower alkylenedioxy or arylenedioxy provided, however, that when R 4 is other than hydrogen or lower alkyl, R 5 is oxo; n is an integer between 1 and 5 inclusive; which process comprises reacting a compound of the formula ##SPC16## wherein R 1 and n are as above with a compound of the formula ##STR13## wherein R 2 is as above in a neutral or slightly acidic aqueous solvent medium in the absence of a base catalyst.
Claim 6
Dependent Claim
167 words
A process for the preparation of a compound of the formula ##STR11## wherein R 1 is lower alkyl, aryl, aralkyl, acylamino, lower alkenyl, lower alkynyl, halogen, lower alkanoyloxy, or lower alkoxy carbonyl; R 2 is hydrogen, lower alkyl, aryl, aralkyl and -(CH 2 ) p R 3 where p is an integer between 0 and 2 inclusive and R 3 is halogen, hydroxy, lower alkoxy, mesyloxy, tosyloxy, cyano or ##STR12## where R 4 is hydrogen, hydroxy, lower alkyl, lower alkoxy, aryloxy and aryl lower alkoxy and R 5 is oxo, lower alkylenedioxy or arylenedioxy provided, however, that when R 4 is other than hydrogen or lower alkyl, R 5 is oxo; n is an integer between 1 and 5 inclusive; which process comprises reacting a compound of the formula ##SPC16## wherein R 1 and n are as above with a compound of the formula ##STR13## wherein R 2 is as above in a neutral or slightly acidic aqueous solvent medium in the absence of a base catalyst.
Claim 7
Dependent Claim
47 words
A process wherein 2-methyl-cyclopentane-1,3-dione is reacted with methyl vinyl ketone in the presence of water as solvent at a temperature between 5° and 60°C. followed by solvent extraction of the reaction products, evaporation of the solvent and purification of the residue by distillation whereby 2-methyl-2-(3'-oxobutyl)-cyclopentane-1,3-dione is obtained.
Claim 8
Dependent Claim
47 words
A process wherein 2-methyl-cyclopentane-1,3-dione is reacted with methyl vinyl ketone in the presence of water as solvent at a temperature between 5° and 60°C. followed by solvent extraction of the reaction products, evaporation of the solvent and purification of the residue by distillation whereby 2-methyl-2-(3'-oxobutyl)-cyclopentane-1,3-dione is obtained.
Claim 9
Dependent Claim
75 words
A process for the preparation of a compound of the formula ##STR14## where R 1 is lower alkyl, R 2 is hydrogen or lower alkyl, and n is an integer between 1 and 5, inclusive, which process comprises reacting a compound of the formula ##SPC17## where R 1 and n are as above with a compound of the formula ##STR15## where R 2 is as above, in a neutral or slightly acidic aqueous solvent medium.
Claim 10
Dependent Claim
75 words
A process for the preparation of a compound of the formula ##STR14## where R 1 is lower alkyl, R 2 is hydrogen or lower alkyl, and n is an integer between 1 and 5, inclusive, which process comprises reacting a compound of the formula ##SPC17## where R 1 and n are as above with a compound of the formula ##STR15## where R 2 is as above, in a neutral or slightly acidic aqueous solvent medium.
Claim 11
Dependent Claim
18 words
The process of claim 5, wherein R 1 is methyl, R 2 is hydrogen and n is 2.
Claim 12
Dependent Claim
14 words
The process of claim 5 wherein said neutral aqueous solvent medium comprises demineralized water.
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) | 1979-08-17 | 1980-02-16 | 1980-08-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-17 | 1984-02-16 | 1984-08-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-17 | 1988-02-16 | 1988-08-17 | $7700.00 | Window Closed / Lapsed |