PL419123A1 - Chiral pyrrolidinium salts with a fragment of natural terpene and method for obtaining chiral pyrrolidinium salts with a fragment of natural terpene - Google Patents
Chiral pyrrolidinium salts with a fragment of natural terpene and method for obtaining chiral pyrrolidinium salts with a fragment of natural terpeneInfo
- Publication number
- PL419123A1 PL419123A1 PL419123A PL41912316A PL419123A1 PL 419123 A1 PL419123 A1 PL 419123A1 PL 419123 A PL419123 A PL 419123A PL 41912316 A PL41912316 A PL 41912316A PL 419123 A1 PL419123 A1 PL 419123A1
- Authority
- PL
- Poland
- Prior art keywords
- chiral
- fragment
- natural terpene
- pyrrolidinium
- imide
- Prior art date
Links
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title abstract 5
- 239000012634 fragment Substances 0.000 title abstract 4
- 150000003505 terpenes Chemical class 0.000 title abstract 4
- 235000007586 terpenes Nutrition 0.000 title abstract 4
- -1 hept-2-yloxymethyl Chemical group 0.000 abstract 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 abstract 1
- DOYSIZKQWJYULQ-UHFFFAOYSA-N 1,1,2,2,2-pentafluoro-n-(1,1,2,2,2-pentafluoroethylsulfonyl)ethanesulfonamide Chemical compound FC(F)(F)C(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)C(F)(F)F DOYSIZKQWJYULQ-UHFFFAOYSA-N 0.000 abstract 1
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 229910004039 HBF4 Inorganic materials 0.000 abstract 1
- 229910004713 HPF6 Inorganic materials 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 125000000129 anionic group Chemical group 0.000 abstract 1
- 125000002091 cationic group Chemical group 0.000 abstract 1
- 150000003949 imides Chemical class 0.000 abstract 1
- 229910003002 lithium salt Inorganic materials 0.000 abstract 1
- 159000000002 lithium salts Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Landscapes
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem zgłoszenia jest chiralna sól pirolidyniowa z fragmentem naturalnego terpenu, o wzorze przedstawionym na rysunku, która ma w części kationowej, przy czwartorzędowym atomie azotu, chiralny podstawnik [(1S, 2R, 4S)-1,7,7-trimetylobicyclo[2.2.1]hept-2-yloksymetylowy, zaś część anionową stanowi anion heksafluorofosforanowy lub tetrafluoroboranowy lub trifluorometanosulfonianowy lub bis(trifluorometylosulfonylo)imidkowy lub bis(pentafluoroetylosulfonylo)imidkowy lub perfluorobutanosulfonianowy. Przedmiotem zgłoszenia jest też sposób wytwarzania chiralnej soli pirolidyniowej z fragmentem naturalnego terpenu, który charakteryzuje się tym, że chlorek N-(2-hydroksyetylo)-N-[(1S,2R,4S)-1,7,7-trimetylobicyclo[2.2.1]hept-2-yloksymetylo]-pirolidyniowy poddaje się reakcji z solą sodową lub potasową lub litową kwasu HPF6 lub HBF4 lub HOSO2CF3 lub HN(SO2CF3)2 lub HN(SO2C2F5)2 lub HOSO2C4F9 zastosowaną w ilości równomolowej lub z nadmiarem do 5% molowych w środowisku wody lub w mieszaninie wody i chlorku metylenu. Reakcję prowadzi się w temperaturze 20°C - 60°C, w czasie od 6 do 24 godzin, wytwarzając chiralną sól pirolidyniową o wzorze z rysunku, gdzie X oznacza anion heksafluorofosforanowy lub tetrafluoroboranowy lub trifluorometanosulfonianowy lub bis(trifluorometylosulfonylo)imidkowy lub bis(pentafluoroetylosulfonylo)imidkowy lub perfluorobutanosulfonianowy.The subject of the application is a chiral pyrrolidinium salt with a fragment of natural terpene, with the formula shown in the figure, which has in the cationic part, at the quaternary nitrogen atom, a chiral substituent [(1S, 2R, 4S) -1,7,7-trimethylbicyclo [2.2.1 ] hept-2-yloxymethyl, and the anionic part is a hexafluorophosphate or tetrafluoroborate or trifluoromethanesulfonate or bis (trifluoromethylsulfonyl) imide or bis (pentafluoroethylsulfonyl) imide or perfluorobutane sulfonate anion. The subject of the application is also a method for producing the chiral pyrrolidinium salt with a fragment of natural terpene, which is characterized by the fact that N- (2-hydroxyethyl) -N - [(1S, 2R, 4S) -1,7,7-trimethylbicyclo chloride [2.2. 1] hept-2-yloxymethyl] -pyrrolidinium is reacted with the sodium or potassium or lithium salt of HPF6 or HBF4 or HOSO2CF3 or HN (SO2CF3) 2 or HN (SO2C2F5) 2 or HOSO2C4F9 used in an equimolar amount or with an excess of 5% molar in water or in a mixture of water and methylene chloride. The reaction is carried out at 20 ° C - 60 ° C for 6 to 24 hours, producing a chiral pyrrolidinium salt of the formula in the figure, wherein X is a hexafluorophosphate or tetrafluoroborate anion or trifluoromethanesulfonate or bis (trifluoromethylsulfonyl) imide sulfonyl or phenyl (bis) imide or perfluorobutane sulfonate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL419123A PL232151B1 (en) | 2016-10-17 | 2016-10-17 | Chiral pyrrolidinium salts with a fragment of natural terpene and method for obtaining chiral pyrrolidinium salts with a fragment of natural terpene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL419123A PL232151B1 (en) | 2016-10-17 | 2016-10-17 | Chiral pyrrolidinium salts with a fragment of natural terpene and method for obtaining chiral pyrrolidinium salts with a fragment of natural terpene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL419123A1 true PL419123A1 (en) | 2018-04-23 |
| PL232151B1 PL232151B1 (en) | 2019-05-31 |
Family
ID=61965326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL419123A PL232151B1 (en) | 2016-10-17 | 2016-10-17 | Chiral pyrrolidinium salts with a fragment of natural terpene and method for obtaining chiral pyrrolidinium salts with a fragment of natural terpene |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL232151B1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL422398A1 (en) * | 2017-07-31 | 2019-02-11 | Zachodniopomorski Uniwersytet Technologiczny W Szczecinie | Chiral pyrrolidinium salt with a fragment of natural terpene and method for producing chiral pyrrolidinium salt with a fragment of natural terpene |
| PL422399A1 (en) * | 2017-07-31 | 2019-02-11 | Zachodniopomorski Uniwersytet Technologiczny W Szczecinie | Chiral pyrrolidinium salts with a fragment of natural terpene and method for producing chiral pyrrolidinium salts with a fragment of natural terpene |
-
2016
- 2016-10-17 PL PL419123A patent/PL232151B1/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL422398A1 (en) * | 2017-07-31 | 2019-02-11 | Zachodniopomorski Uniwersytet Technologiczny W Szczecinie | Chiral pyrrolidinium salt with a fragment of natural terpene and method for producing chiral pyrrolidinium salt with a fragment of natural terpene |
| PL422399A1 (en) * | 2017-07-31 | 2019-02-11 | Zachodniopomorski Uniwersytet Technologiczny W Szczecinie | Chiral pyrrolidinium salts with a fragment of natural terpene and method for producing chiral pyrrolidinium salts with a fragment of natural terpene |
Also Published As
| Publication number | Publication date |
|---|---|
| PL232151B1 (en) | 2019-05-31 |
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