PL417181A1 - Chiral pyrrolidinium salt and method for producing the chiral pyrrolidinium salt - Google Patents
Chiral pyrrolidinium salt and method for producing the chiral pyrrolidinium saltInfo
- Publication number
- PL417181A1 PL417181A1 PL417181A PL41718116A PL417181A1 PL 417181 A1 PL417181 A1 PL 417181A1 PL 417181 A PL417181 A PL 417181A PL 41718116 A PL41718116 A PL 41718116A PL 417181 A1 PL417181 A1 PL 417181A1
- Authority
- PL
- Poland
- Prior art keywords
- chiral
- bis
- pyrrolidinium
- pyrrolidinium salt
- salt
- Prior art date
Links
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 hexafluorophosphate Chemical group 0.000 abstract 5
- 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 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 2
- 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
- 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
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000129 anionic group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000002091 cationic group Chemical group 0.000 abstract 1
- 229910003002 lithium salt Inorganic materials 0.000 abstract 1
- 159000000002 lithium salts Chemical class 0.000 abstract 1
- 238000000034 method 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
- 239000003960 organic solvent Substances 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)
Abstract
Przedmiotem zgłoszenia jest chiralna sól pirolidyniowa, o przedstawionym wzorze, który ma w części kationowej, przy czwartorzędowym atomie azotu, grupę 2-hydroksyetylową i chiralny podstawnik (1R,2S,5R)-(-)-2-izopropylo-5-metylocykloheksyl-1-oksymetylowy, zaś część anionową stanowi anion heksafluorofosforanowy lub tetrafluoroboranowy lub trifluorometanosulfonianowy lub bis(trifluorometylosulfonylo)imidkowy lub bis(pentafluoroetylosulfonylo)imidkowy. We Wzorze X oznacza PF6-, BF4-, (CF3SO2)2N-, CF3SO3-, (C2F5SO2)2N-. Zgłoszenie zawiera też sposób wytwarzania chiralnej soli pirolidyniowej, która charakteryzuje się tym, że chlorek N-(2-hydroksyetylo)-N-[(1R,2S,5R)-(-)-2-izopropylo-5-metylocykloheksyl-1-oksymetylo]-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, zastosowaną z nadmiarem do 10% molowych, w środowisku wody lub w mieszaninie wody i rozpuszczalnika organicznego, przy czym reakcję prowadzi się w temperaturze 25°C - 40°C, w czasie od 5 do 24 godzin, wytwarzając chiralną sól pirolidyniową o wzorze, gdzie X oznacza anion heksafluorofosforanowy lub tetrafluoroboranowy lub trifluorometanosulfonianowy lub bis(trifluorometylosulfonylo)imidkowy lub bis(pentafluoroetylosulfonylo)imidkowy.The subject of the application is a chiral pyrrolidinium salt, having the formula shown, which has a cationic part, with a quaternary nitrogen atom, a 2-hydroxyethyl group and a chiral substituent (1R, 2S, 5R) - (-) - 2-isopropyl-5-methylcyclohexyl-1 -oxymethyl and the anionic part is a hexafluorophosphate or tetrafluoroborate or trifluoromethanesulfonate or bis (trifluoromethylsulfonyl) imide or bis (pentafluoroethylsulfonyl) imion anion. In Formula X is PF6-, BF4-, (CF3SO2) 2N-, CF3SO3-, (C2F5SO2) 2N-. The application also contains a process for the preparation of a chiral pyrrolidinium salt, which is characterized in that N- (2-hydroxyethyl) -N - [(1R, 2S, 5R) - (-) - 2-isopropyl-5-methylcyclohexyl-1-oxymethyl chloride ] - 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, used in excess of 10 mol%, in water or in a mixture of water and an organic solvent wherein the reaction is carried out at a temperature of 25 ° C - 40 ° C for 5 to 24 hours to form a chiral pyrrolidinium salt of formula where X is a hexafluorophosphate or tetrafluoroborate anion or trifluoromethanesulfonate or bis (trifluoromethylsulfonyl) imide sulfide or bis (phenyl) ) imidkowy.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL417181A PL232006B1 (en) | 2016-05-13 | 2016-05-13 | Chiral pyrrolidinium salt and method for producing the chiral pyrrolidinium salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL417181A PL232006B1 (en) | 2016-05-13 | 2016-05-13 | Chiral pyrrolidinium salt and method for producing the chiral pyrrolidinium salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL417181A1 true PL417181A1 (en) | 2017-11-20 |
| PL232006B1 PL232006B1 (en) | 2019-04-30 |
Family
ID=60324420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL417181A PL232006B1 (en) | 2016-05-13 | 2016-05-13 | Chiral pyrrolidinium salt and method for producing the chiral pyrrolidinium salt |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL232006B1 (en) |
-
2016
- 2016-05-13 PL PL417181A patent/PL232006B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL232006B1 (en) | 2019-04-30 |
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