PL415355A1 - Chiral polycyclic quaternary ammonium salts and method for producing them from the cinchona tree analogs - Google Patents
Chiral polycyclic quaternary ammonium salts and method for producing them from the cinchona tree analogsInfo
- Publication number
- PL415355A1 PL415355A1 PL415355A PL41535515A PL415355A1 PL 415355 A1 PL415355 A1 PL 415355A1 PL 415355 A PL415355 A PL 415355A PL 41535515 A PL41535515 A PL 41535515A PL 415355 A1 PL415355 A1 PL 415355A1
- Authority
- PL
- Poland
- Prior art keywords
- quaternary ammonium
- ammonium salts
- chiral
- analogs
- producing
- Prior art date
Links
- -1 polycyclic quaternary ammonium salts Chemical class 0.000 title abstract 5
- 235000021513 Cinchona Nutrition 0.000 title 1
- 241000157855 Cinchona Species 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 150000001768 cations Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- 229930013930 alkaloid Natural products 0.000 abstract 1
- 150000003797 alkaloid derivatives Chemical class 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Rozwiązanie ujawnia chiralne policykliczne czwartorzędowe sole amoniowe, zawierające kation z nowym sześcioczłonowym pierścieniem pomiędzy atomami 1 i 9 wyjściowego alkaloidu o wzorze ogólnym 1, w którym R2 oznacza, grupę etylową lub winylową, a X- oznacza anion halogenkowy lub fluoroboranowy, znajdujące zastosowanie w asymetrycznej katalizie przeniesienia fazowego. Wynalazek obejmuje również sposób wytwarzania chiralnych policyklicznych czwartorzędowych soli amoniowych o wzorze ogólnym 1, w którym R2 oznacza grupę etylową lub winylową, a X- oznacza anion halogenkowy lub fluoroboranowy, zawierających układ kationu 1-aza-tetracyklo[10.2.2.03,8.0l,l0-]heksadecyliowego. Sposób polega na tym, że 9-(2-hydroksymetylofenylo - pochodną alkaloidu drzewa chinowego poddaje się reakcji z chlorkiem tionylu, przy czym reakcję prowadzi się w rozpuszczalniku organicznym, wybranym z grupy obejmującej rozpuszczalniki chlorowcowane jak chloroform i dichlorometan, a otrzymany produkt jest ogrzewany w zawiesinie.The solution reveals chiral polycyclic quaternary ammonium salts, containing a cation with a new six-membered ring between the atoms 1 and 9 of the starting alkaloid of general formula 1, in which R2 is an ethyl or vinyl group, and X- is a halide or fluoroborane anion used in asymmetric catalysis phase transfer. The invention also includes a process for the preparation of chiral polycyclic quaternary ammonium salts of general formula 1, wherein R2 is an ethyl or vinyl group and X- is a halide or fluoroborate anion containing a 1-aza-tetracyclo cation system [10.2.2.03,8.0l, 10 -] heksadecyliowego. The method consists in the fact that 9- (2-hydroxymethylphenyl - quinine alkaloid derivative is reacted with thionyl chloride, the reaction being carried out in an organic solvent selected from the group consisting of halogenated solvents such as chloroform and dichloromethane, and the obtained product is heated in suspension.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL415355A PL228915B1 (en) | 2015-12-17 | 2015-12-17 | Chiral polycyclic quaternary ammonium salts and method for producing them from the cinchona tree analogs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL415355A PL228915B1 (en) | 2015-12-17 | 2015-12-17 | Chiral polycyclic quaternary ammonium salts and method for producing them from the cinchona tree analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL415355A1 true PL415355A1 (en) | 2016-11-21 |
| PL228915B1 PL228915B1 (en) | 2018-05-30 |
Family
ID=57287973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL415355A PL228915B1 (en) | 2015-12-17 | 2015-12-17 | Chiral polycyclic quaternary ammonium salts and method for producing them from the cinchona tree analogs |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL228915B1 (en) |
-
2015
- 2015-12-17 PL PL415355A patent/PL228915B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL228915B1 (en) | 2018-05-30 |
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