HUP0500373A2 - Process for the production of nipecolic acid ethylester enantiomers - Google Patents
Process for the production of nipecolic acid ethylester enantiomersInfo
- Publication number
- HUP0500373A2 HUP0500373A2 HU0500373A HUP0500373A HUP0500373A2 HU P0500373 A2 HUP0500373 A2 HU P0500373A2 HU 0500373 A HU0500373 A HU 0500373A HU P0500373 A HUP0500373 A HU P0500373A HU P0500373 A2 HUP0500373 A2 HU P0500373A2
- Authority
- HU
- Hungary
- Prior art keywords
- salt
- acid
- nipecotic
- ethylester
- evaporated
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 3
- 125000004494 ethyl ester group Chemical group 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- XIWBSOUNZWSFKU-UHFFFAOYSA-N ethyl piperidine-3-carboxylate Chemical compound CCOC(=O)C1CCCNC1 XIWBSOUNZWSFKU-UHFFFAOYSA-N 0.000 abstract 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- XIWBSOUNZWSFKU-SSDOTTSWSA-N ethyl (3r)-piperidine-3-carboxylate Chemical compound CCOC(=O)[C@@H]1CCCNC1 XIWBSOUNZWSFKU-SSDOTTSWSA-N 0.000 abstract 2
- 239000000706 filtrate Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 229960001367 tartaric acid Drugs 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- XIWBSOUNZWSFKU-ZETCQYMHSA-N ethyl (3s)-piperidine-3-carboxylate Chemical compound CCOC(=O)[C@H]1CCCNC1 XIWBSOUNZWSFKU-ZETCQYMHSA-N 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Racemic nipecotic ethylester and (R,R)-tartaric acid are dissolved in ethyl alcohol. Concentrated hydrochloric acid aqueous solution is added, and diastereomeric salt is filtered. Salt is treated, phases are separated, and organic solvent is evaporated to obtain (R)-nipecotic acid ethylester. Filtrate of diastereomeric salt formation is evaporated, to obtain (S)-nipecotic acid ethylester. (S)-isomer is reacted with achiral acid to obtain salt. Salt of racemic composition is filtered, alkalized, extracted and evaporated, to obtain enantiomer mixture. One mole of racemic nipecotic ethylester and half mole (R,R)-tartaric acid are dissolved in ethyl alcohol. Concentrated aqueous solution of half mole hydrochloric acid is added, and the crystalline diastereomeric salt is filtered at 0[deg]C. The resulting salt is treated by aqueous sodium carbonate solution and ethyl acetate. The phases are separated, and organic solvent is evaporated to obtain (R)-nipecotic acid ethylester. The filtrate of diastereomeric salt formation is evaporated, and nipecotic acid ethylester rich in (S)-isomer is obtained from the residue by similar salt processing. The obtained (S)-isomer is reacted with achiral acid such as maleic acid to obtain salt. The crystallized ethyl-nipecotic maleic acid salt of racemic composition is filtered, and alkalized with an aqueous base followed by extraction and evaporation, to obtain enantiomer mixture having higher (S)-isomer content.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0500373A HUP0500373A2 (en) | 2005-04-08 | 2005-04-08 | Process for the production of nipecolic acid ethylester enantiomers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0500373A HUP0500373A2 (en) | 2005-04-08 | 2005-04-08 | Process for the production of nipecolic acid ethylester enantiomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU0500373D0 HU0500373D0 (en) | 2005-05-30 |
| HUP0500373A2 true HUP0500373A2 (en) | 2007-03-28 |
Family
ID=89985921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0500373A HUP0500373A2 (en) | 2005-04-08 | 2005-04-08 | Process for the production of nipecolic acid ethylester enantiomers |
Country Status (1)
| Country | Link |
|---|---|
| HU (1) | HUP0500373A2 (en) |
-
2005
- 2005-04-08 HU HU0500373A patent/HUP0500373A2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU0500373D0 (en) | 2005-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD9A | Lapse of provisional protection due to non-payment of fees |