PL422398A1 - Chiral pyrrolidinium salt with a fragment of natural terpene and method for producing chiral pyrrolidinium salt with a fragment of natural terpene - Google Patents
Chiral pyrrolidinium salt with a fragment of natural terpene and method for producing chiral pyrrolidinium salt with a fragment of natural terpeneInfo
- Publication number
- PL422398A1 PL422398A1 PL422398A PL42239817A PL422398A1 PL 422398 A1 PL422398 A1 PL 422398A1 PL 422398 A PL422398 A PL 422398A PL 42239817 A PL42239817 A PL 42239817A PL 422398 A1 PL422398 A1 PL 422398A1
- Authority
- PL
- Poland
- Prior art keywords
- fragment
- chiral
- natural terpene
- pyrrolidinium salt
- pyrrolidinium
- Prior art date
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- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Przedmiotem zgłoszenia jest chiralna sól pirolidyniowa z fragmentem naturalnego terpenu, przedstawiona we wzorze ogólnym, która ma w części kationowej, przy czwartorzędowym atomie azotu, chiralny podstawnik [(1R-endo)-1,3,3-trimetylobicyklo[2.2.1]hept-2-yloksy]metylowy, będący fragmentem (+)-fencholu zaś część anionową stanowi anion chlorkowy. Zgłoszenie obejmuje też sposób wytwarzania chiralnej soli pirolidyniowej z fragmentem naturalnego terpenu, polegający na reakcji pochodnej alkoholu terpenowego z N-(2-hydroksyetylo)pirolidyną przy ich stosunku molowym wynoszącym od 1,0 do 1,1 w środowisku bezwodnego eteru dietylowego, w temperaturze 15°C - 30°C w czasie 8 - 24 godzin, charakteryzuje się tym, że prowadzi się reakcję (1R-endo)-2-chlorometoksy-1,3,3-trimetylobicyclo[2.2.1]heptanu (uzyskanego z (+)-fencholu) z N-(2-hydroksyetylo)pirolidyną otrzymując jako produkt chlorek N-(2-hydroksyetylo)-N-[((1R-endo)-1,3,3-trimetylobicyclo[2.2.1]hept-2-yloksy)metylo]pirolidyniowy.The subject of the application is a chiral pyrrolidinium salt with a fragment of natural terpene, represented in the general formula which has in the cationic part, at the quaternary nitrogen atom, a chiral substituent [(1R-endo) -1,3,3-trimethylbicyclo [2.2.1] hept- 2-yloxy] methyl, which is a (+) - fenchol fragment and the anionic part is the chloride anion. The application also includes a method for producing a chiral pyrrolidine salt with a fragment of natural terpene, consisting of the reaction of a terpene alcohol derivative with N- (2-hydroxyethyl) pyrrolidine at their molar ratio of 1.0 to 1.1 in anhydrous diethyl ether at 15 ° C - 30 ° C for 8 - 24 hours, characterized by the reaction (1R-endo) -2-chloromethoxy-1,3,3-trimethylbicyclo [2.2.1] heptane (obtained from (+) -phenchol) with N- (2-hydroxyethyl) pyrrolidine to obtain N- (2-hydroxyethyl) -N - [((1R-endo) -1,3,3-trimethylbicyclo [2.2.1] hept-2- chloride as product yloxy) methyl] pyrrolidinium.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422398A PL237112B1 (en) | 2017-07-31 | 2017-07-31 | Chiral pyrrolidinium salt with a fragment of natural terpene and method for producing chiral pyrrolidinium salt with a fragment of natural terpene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422398A PL237112B1 (en) | 2017-07-31 | 2017-07-31 | Chiral pyrrolidinium salt with a fragment of natural terpene and method for producing chiral pyrrolidinium salt with a fragment of natural terpene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL422398A1 true PL422398A1 (en) | 2019-02-11 |
| PL237112B1 PL237112B1 (en) | 2021-03-22 |
Family
ID=65270328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL422398A PL237112B1 (en) | 2017-07-31 | 2017-07-31 | Chiral pyrrolidinium salt with a fragment of natural terpene and method for producing chiral pyrrolidinium salt with a fragment of natural terpene |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL237112B1 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8961656B2 (en) * | 2010-06-28 | 2015-02-24 | Korea Institute Of Energy Research | Gas hydrate inhibitor and method of inhibiting gas hydrate formation |
| PL417180A1 (en) * | 2016-05-13 | 2017-11-20 | Zachodniopomorski Uniwersytet Technologiczny W Szczecinie | Chiral pyrrolidinium salt and method for producing the chiral pyrrolidinium salt |
| PL419124A1 (en) * | 2016-10-17 | 2018-04-23 | Zachodniopomorski Uniwersytet Technologiczny W Szczecinie | Chiral pyrrolidinium salts with a fragment of natural terpene and method for obtaining chiral pyrrolidinium salts with a fragment of natural terpene |
| PL419123A1 (en) * | 2016-10-17 | 2018-04-23 | Zachodniopomorski Uniwersytet Technologiczny W Szczecinie | Chiral pyrrolidinium salts with a fragment of natural terpene and method for obtaining chiral pyrrolidinium salts with a fragment of natural terpene |
-
2017
- 2017-07-31 PL PL422398A patent/PL237112B1/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8961656B2 (en) * | 2010-06-28 | 2015-02-24 | Korea Institute Of Energy Research | Gas hydrate inhibitor and method of inhibiting gas hydrate formation |
| PL417180A1 (en) * | 2016-05-13 | 2017-11-20 | Zachodniopomorski Uniwersytet Technologiczny W Szczecinie | Chiral pyrrolidinium salt and method for producing the chiral pyrrolidinium salt |
| PL419124A1 (en) * | 2016-10-17 | 2018-04-23 | Zachodniopomorski Uniwersytet Technologiczny W Szczecinie | Chiral pyrrolidinium salts with a fragment of natural terpene and method for obtaining chiral pyrrolidinium salts with a fragment of natural terpene |
| PL419123A1 (en) * | 2016-10-17 | 2018-04-23 | Zachodniopomorski Uniwersytet Technologiczny W Szczecinie | Chiral pyrrolidinium salts with a fragment of natural terpene and method for obtaining chiral pyrrolidinium salts with a fragment of natural terpene |
Also Published As
| Publication number | Publication date |
|---|---|
| PL237112B1 (en) | 2021-03-22 |
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