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Synthesis method of myosmine

A synthesis method and compound technology, applied in organic chemistry, bulk chemical production, etc., can solve the problems of high price of rhodium catalyst, no commercial production, lack of atom economy, etc., and achieve good application prospects and convenient product separation and purification. , the effect of good economic benefits

Pending Publication Date: 2022-06-03
上海锐康生物技术研发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the extraction of mesmin from plants is limited by many factors. Therefore, it is urgent to develop more effective synthetic methods.
[0003] Wiegrebe reported that using 3-acetylpyridine as a starting material, mesmin was synthesized through 5-step reactions including carbonyl protection, intermolecular coupling, deprotection, cyanation, and hydrogenation cyclization. Harsh, and uses highly toxic potassium cyanide (KCN), it is not easy to post-process (Arch.Pharm.1988,321,175-177); Sames reported the use of rhodium to catalyze the cross-coupling of pyridine ring and pyrrole ring to synthesize mesmin , but this method has been subjected to the limitation of factors such as rhodium catalyst price is expensive, yield is low; ethylene, so as to achieve intramolecular condensation and cyclization, and finally get mesmine, but this method needs to remove a part of ethylene, which lacks the corresponding atom economy
[0004] It can be seen that several known preparation methods about mesmin still have deficiencies, and have not been used in commercial production

Method used

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  • Synthesis method of myosmine
  • Synthesis method of myosmine
  • Synthesis method of myosmine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1, the preparation of mesmin

[0057] The reaction formula for preparing Mesmin by 3-pyridinecarboxaldehyde is as follows:

[0058]

[0059] Under nitrogen conditions, add iodine (0.01 mmol) and 3-bromopropionitrile (7.0 mmol) to the three-necked flask and dissolve in tetrahydrofuran (THF), place in an ice-water bath, add magnesium turnings (5.5 mmol) until the magnesium turnings dissolve, then , under the condition of ice-water bath, 3-pyridinecarboxaldehyde (5.0mmol) was slowly added dropwise to react for 2 hours, saturated ammonium chloride solution (20mL) was added to quench the reaction, ethyl acetate (20mL*3) was extracted, dried and concentrated to obtain the crude product , the crude product was dissolved in a single-necked flask with DCM, active manganese dioxide (60.0 mmol) was added and stirred at room temperature for 10 hours, filtered, and the filtrate was concentrated and spin-dried to obtain crude product 3, which was directly used in the ne...

Embodiment 2

[0061] Embodiment 2, the preparation of mesmin

[0062] Taking 3-pyridinecarboxaldehyde as raw material to prepare Maismin, the concrete method is as follows:

[0063] Under nitrogen conditions, iodine (0.01 mmol) and 3-bromopropionitrile (6.0 mmol) were added to the three-necked flask and dissolved in ether, placed in an ice-water bath, and magnesium turnings (6.0 mmol) were added until the magnesium turnings were dissolved. Under water bath conditions, 3-pyridinecarbaldehyde (5.0 mmol) was slowly added dropwise to react for 2 hours, saturated ammonium chloride solution (20 mL) was added to quench the reaction, extracted with ethyl acetate (20 mL*3), dried, and concentrated to obtain the crude product. Dissolve in a single-necked flask with DCM, add active manganese dioxide (50.0 mmol) and stir at room temperature for 10 hours, filter, concentrate the filtrate and spin dry to obtain crude product 3, which is directly used in the next reaction.

[0064] The crude product 3 wa...

Embodiment 3

[0065] Embodiment 3, the preparation of mesmin

[0066] Taking 3-pyridinecarboxaldehyde as raw material to prepare Maismin, the concrete method is as follows:

[0067] Under nitrogen conditions, add iodine (0.01 mmol) and 3-bromopropionitrile (6.0 mmol) to the three-necked flask and dissolve in THF, place in an ice-water bath, add magnesium turnings (6.5 mmol) until the magnesium turnings are dissolved, then, in ice Under water bath conditions, 3-pyridinecarbaldehyde (5.0 mmol) was slowly added dropwise to react for 3 hours, saturated ammonium chloride solution (20 mL) was added to quench the reaction, extracted with ethyl acetate (20 mL*3), dried, and concentrated to obtain the crude product. Dissolve in a single-necked flask with DCM, add active manganese dioxide (55.0 mmol) and stir at room temperature for 10 hours, filter, concentrate the filtrate and spin dry to obtain crude product 3, which is directly used in the next reaction.

[0068] The crude product 3 was added to...

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Abstract

The invention provides a synthesis method of myosmine, and belongs to the technical field of chemical engineering. According to the synthesis method, a pyridine aldehyde ketone compound 1 and a brominated nitrile compound 2 are used as raw materials, and the myosmine is synthesized through coupling cyclization. The synthesis method comprises the following steps: (1) under an alkaline condition, carrying out a coupling reaction on a pyridine aldehyde ketone compound 1 and a brominated nitrile compound 2 in a solvent to generate a compound 3; (2) in a solvent, carrying out series hydrogenation cyclization reaction on the compound 3 under the action of a hydrogen source and a catalyst to synthesize myosmine 4; r is selected from hydrogen and methane; n is selected from 0 or 1. The synthesis method provided by the invention has the advantages of easily available raw materials, simple synthesis steps, mild reaction conditions, convenient product separation and purification, and high product yield and purity; compared with the existing method for synthesizing the myosmin, the method has the advantages of low cost, high efficiency and good product quality. The synthesis method has the possibility of large-scale production, is expected to be commercialized in production, and has a good application prospect and expected economic benefits.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and particularly relates to a method for synthesizing mesmin. Background technique [0002] High-purity nicotine has important potential applications in the fields of medicine, pesticides and health care. Mesmin is often used as an important intermediate in the synthesis of nicotine and has a wide range of market application prospects (DOI: 10.1016 / B978-044450095-3 / 50014-0 , chapter 13). In addition, mesmin has always been considered as a special tobacco alkaloid, widely present in many plants, especially nut products are an important source of mesmin (J.Agric.Food Chem.2002,50,4909- 4915). However, the extraction of mesmin from plants is limited by many factors. Therefore, it is urgent to develop a more effective synthetic method. [0003] Wiegrebe reported that 3-acetylpyridine was used as the starting material to synthesize mesmin through five steps of carbonyl protection, intermo...

Claims

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Application Information

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IPC IPC(8): C07D401/04
CPCC07D401/04Y02P20/55
Inventor 王圣克张磊李正华赵华
Owner 上海锐康生物技术研发有限公司
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