- Preparation method of optically pure lobeline hydrochloride and enantiomer thereof
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The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of optically pure lobeline hydrochloride and an enantiomer of the optically pure lobeline hydrochloride. According to the method, benzoylacetic acid, methylamine hydrochloride and glutaraldehyde are used as raw materials, and a target product can be prepared through condensation, reduction, acylation, resolution, oxidation and hydrolysis reactions in sequence. According to the method, meso-racemic lobeline is derived into raceme through acylation by adopting a desymmetry strategy, so that conditions are created for further resolution, and the use of a chiral catalyst which is high in price and tedious in preparation is avoided. In the splitting step, the product is filtered, the obtained filtrate is subjected to hydrolysis and other treatments to obtain an intermediate compound II, and the intermediate compound II can be recycled, so that the process cost is greatly saved; and moreover, the whole preparation process flow is simple to operate, mild in condition, high in optical purity of the product and very suitable for large-scale industrial production.
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Paragraph 0041-0042; 0045
(2021/11/03)
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- Synthesis of (-)-lobeline via enzymatic desymmetrization of lobelanidine
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The bioactive alkaloid (-)-lobeline was synthesized via the stereoselective acylation (desymmetrization) of meso-lobelanidine by vinyl acetate in the presence of Candida antarctica lipase B.
- Chenevert, Robert,Morin, Pierre
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experimental part
p. 1837 - 1839
(2009/05/26)
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- Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: Applications to the total synthesis of alkaloids
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Enantioselective syntheses of the alkaloids (-)-aurantioclavine, (+)-amurensinine, (-)-lobeline, and (-)- and (+)-sedamine are described. The syntheses demonstrate the effectiveness of the Pd-catalyzed asymmetric oxidation of secondary alcohols in diverse contexts and the ability of this methodology to set the absolute configuration of multiple stereocenters in a single operation. The utility of an aryne C-C insertion reaction in accessing complex polycyclic frameworks is also described.
- Krishnan, Shyam,Bagdanoff, Jeffrey T.,Ebner, David C.,Ramtohul, Yeeman K.,Tambar, Uttam K.,Stoltz, Brian M.
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supporting information; experimental part
p. 13745 - 13754
(2009/02/06)
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- Enantioselective synthesis of lobeline via nonenzymatic desymmetrization
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Lobeline has been prepared in enantiopure form via desymmetrization of lobelanidine with use of BTM, a nonenzymatic enantioselective acyl transfer catalyst.
- Birman, Vladimir B.,Jiang, Hui,Li, Ximin
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p. 3237 - 3240
(2008/02/11)
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- 2,6-disubstituted piperidines as modulators of nicotinic acetylcholine receptor mediated neurotransmitter release, uptake and storage
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Compounds used for treating dependence on or withdrawal from a drug of abuse, for an eating disorder or for a CNS disease or pathology having the following formulas:
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Page column 5-6
(2008/06/13)
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- USE OF NAFION MEMBRANES IN LABORATORY ORGANIC ELECTROSYNTHESIS
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Electrolysis of quarternary ammonium bromides and iodides in a divided cell with a Nafion membrane yields quarternary polyhalogenides at a carbon anode in water-ethanolic anolytes.The electrodialysis of tetrabutylammonium iodide in a cell with a Nafion membrane enables generation of tetrabutylammonium hydroxide.In electrolytic reduction of nitrobenzene in presence of 1,3-dibromopropane, N-phenylisoxazolidine results in approx. 60percent yield.This electrosynthesis takes place in dimethylformamide with tetrabutylammonium bromide at a glassy-carbon cathode in a divided cell.In the electroreduction of lobelanine hydrogensulfate in a divided cell in acid water-ethanolic media at a lead cathode prevalently lobelanidine has been obtained.
- Hlavaty, Jaromir,Volke, Jiri
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p. 3164 - 3170
(2007/10/02)
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