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Method for synthesizing 2-(2- fluoropyridine-3-yl) C-2-alcohol and monohydrate crystal

A synthesis method and fluoropyridine technology, applied in the direction of organic chemistry and the like, can solve the problems of inconvenient industrial production, low product purity, reduced reaction yield, etc., and achieve the effects of easy purification, good selectivity and simple purification method.

Inactive Publication Date: 2009-08-12
EAST CHINA NORMAL UNIV
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  • Abstract
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Problems solved by technology

[0007] The generation of above-mentioned by-products can lead to the reduction of reaction yield, and the yield of reaction is only 30-40%
And because the structure of the by-product is similar to that of the main product, column chromatography is used for the separation and purification of the main product. This method has high cost, low product purity, and is not easy to realize industrial production.

Method used

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  • Method for synthesizing 2-(2- fluoropyridine-3-yl) C-2-alcohol and monohydrate crystal
  • Method for synthesizing 2-(2- fluoropyridine-3-yl) C-2-alcohol and monohydrate crystal
  • Method for synthesizing 2-(2- fluoropyridine-3-yl) C-2-alcohol and monohydrate crystal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] in N 2 Under the atmosphere, dissolve diisopropylamine (0.688mol) in tetrahydrofuran or diethyl ether (625mL), cool to -78~-55°C, add n-butyllithium in n-hexane (2.5mol / L) (0.688mol ) into the reaction system, control the temperature within the range of -78 to -55°C, stir for 1 hour, add 2-fluoropyridine (0.625mol) into the reaction system, and control the temperature within the range of -78 to -55°C , after stirring for 4 hours, add acetone (0.860mol) into the reaction system, control the temperature in the range of -78~-55°C, stir for 0.5 hours, then add saturated ammonium chloride solution (300mL) to the reaction system to quench Reaction, liquid separation, adding saturated sodium chloride (300mL) solution to the organic phase to wash, liquid separation, and rotary evaporation under reduced pressure to remove the solvent to obtain the crude product, which was distilled under reduced pressure (50-60Pa, 65-70°C) The pure product 2-(2-fluoropyridin-3-yl)propan-2-ol wa...

Embodiment 2

[0030] in N 2 Under the atmosphere, dissolve diisopropylamine (0.938mol) in tetrahydrofuran or ether (625mL), cool down to -78~-55℃, and add n-butyllithium in n-hexane (2.5mol / L) (0.938mol ) into the reaction system, control the temperature within the range of -78 to -55°C, stir for 1 hour, add 2-fluoropyridine (0.625mol) into the reaction system, and control the temperature within the range of -78 to -55°C , after stirring for 4 hours, add acetone (0.860mol) into the reaction system, control the temperature in the range of -78~-55°C, stir for 0.5 hours, then add saturated ammonium chloride solution (300mL) to the reaction system to quench Reaction, liquid separation, adding saturated sodium chloride (300mL) solution to the organic phase to wash, liquid separation, and rotary evaporation under reduced pressure to remove the solvent to obtain the crude product, which was distilled under reduced pressure (50-60Pa, 65-70°C) The pure product 2-(2-fluoropyridin-3-yl)propan-2-ol wa...

Embodiment 3

[0032] in N 2 Under the atmosphere, dissolve diethylamine (0.688mol) in tetrahydrofuran or diethyl ether (625mL), cool down to -78~-55°C, add n-butyllithium in n-hexane (2.5mol / L) (0.688mol) Add to the reaction system, control the temperature range in the range of -78 ~ -55 ° C, stir for 1 hour, add 2-fluoropyridine (0.625mol) into the reaction system, control the temperature range in the range of -78 ~ -55 ° C, After stirring for 4 hours, add acetone (0.860mol) to the reaction system, control the temperature within the range of -78 to -55°C, stir for 0.5 hours, then add saturated ammonium chloride solution (300mL) to the reaction system to quench the reaction , liquid separation, adding saturated sodium chloride (300mL) solution to the organic phase for washing, liquid separation, and rotary evaporation under reduced pressure to remove the solvent to obtain a crude product, which was obtained by distillation under reduced pressure (50~60Pa, 65~70°C) Pure product 2-(2-fluorop...

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Abstract

The invention relates to a synthesizing method of 2-(2-fluoro-pyridine-3-yl) C-2-ol and momo-hydrate crystal thereof. 2-fluoro-pyridine and acetone are used as raw materials, n-butyl lithium amine prepared from organic amine and n-butyl lithium is used as alkali, and tetrahydrofuran or aether is solvent. After one-step reaction, saturated ammonium chloride water solution is used for quenching reaction, then sodium chloride solution is used for washing, and solvent is removed through reduced pressure distillation so as to obtain a crude product. The product is obtained through reduced pressure distillation and purification and then dissolved in petroleum ether or n-hexane; water is added while stirring is carried out simultaneously; and the momo-hydrate crystal of the 2-(2-fluoro-pyridine-3-yl) C-2-ol is obtained by means of suction filtration. The mol ratio of the used materials, i.e. the organic amine, the n-butyl lithium, the 2-fluoro-pyridine, the acetone, the tetrahydrofuran or aether is 1 : 1 : 0.7- 0.9 : 0.8-1.2 : 15-20; and the mol ratio of the 2-(2-fluoro-pyridine-3-yl) C-2-ol, the water and the petroleum ether or n-hexane is 1 : 1-1.2 : 15-20. The invention has the advantages of high selectivity, high yield rate, low cost, simple purification method, high purity of the momo-hydrate crystal of the 2-(2-fluoro-pyridine-3-yl) C-2-ol, and convenient storage; and the drug effect can be effectively improved when the 2-(2-fluoro-pyridine-3-yl) C-2-ol and the momo-hydrate crystal thereof are used for preparing drugs.

Description

technical field [0001] The invention relates to a synthesis method of 2-(2-fluoropyridin-3-yl)propan-2-ol and its monohydrate crystal. It belongs to the technical field of pharmaceutical synthesis and chemical engineering. Background technique [0002] Organic fluorine compounds are widely used in the field of medicine. When fluorine atoms are introduced into physiologically active organic compounds, their properties will change drastically. From the discovery that fluorine-containing organic compounds have physiologically active effects, people can exert excellent synergistic effects by introducing fluorine atoms into specific positions of the compounds, thereby promoting the production of various physiologically active drugs such as fluorine medicines and fluorine pesticides. Since the introduction of fluorine atoms into medicines increases the efficacy of medicines, the amount of medicines administered to patients can be reduced, and the side effects are also reduced. T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61
Inventor 厉铭胡文浩史滔达郭震球杨琍苹
Owner EAST CHINA NORMAL UNIV
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