Asymmetric synthesis method for botanical pesticide nicotine and anabasine

A technology of botanical pesticides and anabasine, applied in the direction of organic chemistry, can solve the problems of heavy post-processing workload and high cost of chiral separation methods, and achieve the effects of low cost, stable operation and high purity

Active Publication Date: 2015-02-11
NANKAI UNIV
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Problems solved by technology

However, the cost of chiral resolution method is

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  • Asymmetric synthesis method for botanical pesticide nicotine and anabasine
  • Asymmetric synthesis method for botanical pesticide nicotine and anabasine
  • Asymmetric synthesis method for botanical pesticide nicotine and anabasine

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[0019] The present invention will be described in further detail below through examples, which do not limit the protection scope of the present invention.

[0020] For the experimental methods that do not indicate specific conditions in the examples, usually follow the conventional conditions and the conditions described in the manual, or according to the conditions suggested by the manufacturer; the materials, reagents, etc. used, if no special instructions, can be purchased from commercial sources. get.

[0021] 1) Synthesis of intermediates 1 and 2

[0022] In a three-neck round bottom flask, 2,5-dibromopyridine (2.37 g, 10 mmol) was added under argon protection and dissolved in 25 ml of ether. The solution was stirred and cooled to -78°C, then slowly added dropwise n-BuLi n-hexane solution (1.6M, 7.5ml), kept at -78°C during the dropwise addition, continued to stir at -78°C for 30min after the dropwise addition, and then slowly dropped Add 1-Boc-2-pyrrolidone (1.85g, 10m...

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Abstract

The invention relates to an asymmetric synthesis method for botanical pesticide nicotine and anabasine. The low-cost and easily acquired 2,5-dibromopyridine is taken as an initial raw material and is processed in two steps, so that the hydrogenation precursor annular imine is acquired; under the induction of the chiral catalyst, iridium-phosphine oxazoline, an important hydrogenated product intermediate is acquired through high enantioselectivity; the intermediate is processed in two steps, so that L-nicotine is acquired; the intermediate is converted into L-anabasine in one step. The asymmetric hydrogenation of the annular imine containing pyridine gene is taken as the key step of the method. According to the invention, the chiral catalyst, iridium-phosphine oxazoline, is used for catalyzing the asymmetric hydrogenation and the key intermediate with ultrahigh ee value is acquired, and then the methylation and reduction bromine-removing two-step reaction is performed for converting, so that the target products, natural nicotine and anabasine, are acquired. According to the invention, the operation is stable, the purity is high and the cost is low.

Description

technical field [0001] The invention relates to an asymmetric synthesis method of botanical pesticides nicotine and anabasine. The asymmetric hydrogenation of cyclic imines containing pyridine groups is a key step in the invention. Background technique [0002] Natural nicotine (left-handed) is a chiral amine alkaloid containing a pyridine ring and a tetrahydropyrrole ring. It was first isolated in 1828 and first synthesized by Pictet in 1904. Due to its special structure, it has shown unique biological activity in both pesticides and medicines. It can be used as an insecticide in pesticides, and it can be used as a classic nicotinic acetylcholine receptor in medicine to treat Alzheimer's disease, Pain Other central nervous system disorders such as Kinson's disease, schizophrenia, and depression. Anabasine, also known as neonicotinoid, has similar biological activity to nicotine and has a certain insecticidal effect. [0003] According to research, scientists generally bel...

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Application Information

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IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 徐效华郭翠谢龙观朱守非
Owner NANKAI UNIV
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