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Continuous synthesis method of 1,1'-bicyclo[1.1.1]pentane-1,3-diethyl ketone organic substance

A diethyl ketone, chemical synthesis technology, applied in the field of pharmaceutical intermediate synthesis, can solve the problems of low conversion rate of reaction raw materials, low product yield, unstable reaction raw materials and products, etc., and achieve short reaction time and high product quality. The effect of large yield and reduced probability of decomposition and deterioration

Inactive Publication Date: 2019-09-06
JILIN ASYMCHEM LAB CO LTD
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AI Technical Summary

Problems solved by technology

[0006] The main purpose of the present invention is to provide a continuous synthesis method of 1,1'-bicyclo[1.1.1]pentane-1,3-diethyl ketones to solve the existing 1,1'- During the synthesis of bicyclo[1.1.1]pentane-1,3-diethyl ketone, the reaction raw materials and products are unstable, which leads to the low conversion rate of reaction raw materials and low product yield.

Method used

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  • Continuous synthesis method of 1,1'-bicyclo[1.1.1]pentane-1,3-diethyl ketone organic substance
  • Continuous synthesis method of 1,1'-bicyclo[1.1.1]pentane-1,3-diethyl ketone organic substance
  • Continuous synthesis method of 1,1'-bicyclo[1.1.1]pentane-1,3-diethyl ketone organic substance

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preparation example Construction

[0030] The above continuous synthesis method includes: under the irradiation of light source, the raw material A and raw material B are continuously transported to the continuous reaction device for continuous photochemical reaction to obtain 1,1'-bicyclo[1.1.1]pentane- 1,3-Diethyl ketone is an organic substance, and in the continuous photochemical reaction process, a temperature control device is used to control the reaction temperature in the continuous reaction device, wherein the raw material A has the structure shown in formula (I), and the raw material B Has the structure shown in formula (II):

[0031] R 1 , R 2 , R 3 are independently selected from hydrogen, benzyl, alkyl, aryl, halogen, ester, carboxyl or hydroxyl, and R 1 , R 2 , R 3 at least one of which is not hydrogen; R 4 and R 5 are independently selected from hydrogen, alkyl or aryl.

[0032] The free radicals formed by propeller alkanes with substituents have high stability, so using propeller alka...

Embodiment 1

[0047] Homemade 2-methyl-2-phenyl [1.1.1.0 1,3 ] Propellane n-butyl ether solution 1.56kg, (NMR content 5.0%, conversion raw material 78g) joins in the first feeding device; 2,3-butanedione 143g (1.1equiv.), 200ml cosolvent ethanol joins In the second feeding device, it is prepared into a uniform solution; turn on the light source (the LED lamp with a wavelength of 313nm), open the automatic feeding system, control the plunger pump raw material A solution at 10g / min, 2,3-butanedione ethanol solution Enter the online mixer at 1.93g / min and then enter the continuous reaction device (coil) for reaction. The temperature of the external bath is controlled at 0-5°C, and the retention time is 15 minutes. The product was crystallized and filtered on-line at -55 to -60°C with temperature control, and the white solid was 145.8 g, with a yield of 94%.

Embodiment 2

[0049] The difference from Example 1 is that the temperature of the external bath is 20°C.

[0050] Homemade 2-methyl-2-phenyl [1.1.1.0 1,3 ] Propellane n-butyl ether solution 1.56kg, (NMR content 5.0%, conversion raw material 78g) joins in the first feeding device; 2,3-butanedione 143g (1.1equiv.), 200ml cosolvent ethanol joins In the second feeding device, it is prepared into a uniform solution; turn on the light source (the LED lamp with a wavelength of 313nm), open the automatic feeding system, control the plunger pump raw material A solution at 10g / min, 2,3-butanedione ethanol solution Enter the online mixer at 1.93g / min and then enter the continuous reaction device (coil) for reaction. The temperature of the external bath is controlled at 20°C, and the retention time is 15min. Temperature -55 ~ -60 ℃ online crystallization and filtration product, white solid 120.98g, yield 78%.

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Abstract

The invention provides a continuous synthesis method of 1,1'-bicyclo[1.1.1]pentane-1,3-diethyl ketone organic substance. The continuous synthesis method comprises the steps of under the irradiation ofa light source, continuously conveying a raw material A and a raw material B into a continuous reaction device for a continuous photochemical reaction to obtain the 1,1'-bicyclo[1.1.1]pentane-1,3-diethyl ketone organic substance with a structure shown in a formula (III); using a temperature control device for controlling the reaction temperature in the continuous reaction device, wherein the rawmaterial A has a structure shown in a formula (I), and the raw material B has a structure shown in a formula (II). By adopting propellane with substituents as a reaction raw material and carrying outthe photochemical reaction in the continuous reaction device, the probability of slow decomposition and deterioration of the propellane under illumination can be lowered, and the conversion rate of the reaction raw materials and the product yield are greatly increased.

Description

technical field [0001] The invention relates to the field of synthesis of pharmaceutical intermediates, in particular to a continuous synthesis method of 1,1'-bicyclo[1.1.1]pentane-1,3-diethylketone organic compounds. Background technique [0002] As an unnatural amino acid, 1-aminobicyclo[1.1.1]pentane-1-carboxylate has great potential in medicinal chemistry research, but it is expensive. 1,1'-bicyclo[1.1.1]pentane-1,3-diethylketone is an important intermediate for the synthesis of 1-aminobicyclo[1.1.1]pentane-1-carboxylic acid, and is also an important intermediate for the synthesis of various symmetric The building blocks of propane derivatives can be further functionalized to obtain a series of propane derivatives such as acids, esters, alcohols and amides. Due to the particularity of the substrate, there are few reports on the synthesis of 1,1'-bicyclo[1.1.1]pentane-1,3-diethylketone. [0003] The existing synthesis methods are all batch synthesis methods, using propa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/68C07C49/323C07C49/35
CPCC07C45/68C07C2603/58C07C49/323C07C49/35
Inventor 洪浩张恩选卢江平魏福亮杨思航车冠达
Owner JILIN ASYMCHEM LAB CO LTD
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