Method for synthesizing chiral cyproconazole

A synthesis method and cyproconazole technology are applied in the field of synthesis technology of pesticide cyproconazole, can solve problems such as consumption increase, and achieve the effects of high production cost, improved unit efficacy and high optical purity

Active Publication Date: 2010-08-11
合肥华纳生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The former needs to consume an equivalent amount of chiral resolving agent when synthesizing drugs,

Method used

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  • Method for synthesizing chiral cyproconazole
  • Method for synthesizing chiral cyproconazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] 1) 1-(4-chlorophenyl)-2-cyclopropyl-1-propene A

[0051]Dissolve 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone (20.8g, 100mmol) in pre-dried toluene, keep the temperature at -20°C, and add the pre-prepared In the toluene solution of methylenetriphenylphosphorous ylide (41.5g, 150mmol, 1mol / L), after the dropwise addition was completed, the temperature was slowly raised to room temperature, stirred at room temperature for 6 hours, and the raw material 1-(4-chlorobenzene When the content of -2-cyclopropyl-1-propanone is less than 1%, the reaction ends, and 0.6mol of water is added to the reaction system to quench the reaction. Distilled under reduced pressure to obtain 19.5 g of 1-(4-chlorophenyl)-2-cyclopropyl-1-propene with a yield of 95%.

[0052] 2) Synthesis of epoxidized intermediate B

[0053] 1-(4-Chlorophenyl)-2-cyclopropyl-1-propene A (20.6g, 100mmol) and catalytic amount of titanium tetraisopropoxide (5×10 -4 mol) was dissolved in DMF, keeping the temperature...

Embodiment 2

[0057] 1) Synthesis of 1-(4-chlorophenyl)-2-cyclopropyl-1-propene A

[0058] Dissolve 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone (20.8g, 100mmol) in pre-dried dioxane, keep the temperature at -10°C, add dropwise to the system In the prepared dioxane solution of methylenetriphenylphosphorous ylide (55.3g, 200mmol, 1mol / L), after the dropwise addition was completed, the temperature was slowly raised to room temperature, stirred at room temperature for 8 hours, and the raw material 1 was analyzed by gas chromatography. The content of -(4-chlorophenyl)-2-cyclopropyl-1-propanone is less than 1%. After the reaction is completed, 1 mol of water is added to the reaction system to quench the reaction. Distilled under reduced pressure to obtain 19.2 g of 1-(4-chlorophenyl)-2-cyclopropyl-1-propene, with a yield of 93.1%.

[0059] 2) Synthesis of epoxidized intermediate B

[0060] 1-(4-Chlorophenyl)-2-cyclopropyl-1-propene A (20.6g, 100mmol) and a catalytic amount of salen-Mn (1×10 -...

Embodiment 3

[0064] 1) Synthesis of 1-(4-chlorophenyl)-2-cyclopropyl-1-propene A

[0065] Dissolve 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone (20.8g, 100mmol) in pre-dried THF, keep the temperature at 0°C, and add the pre-prepared In the THF solution of methyltriphenylphosphorus ylide (82.8g, 300mmol, 1mol / L), after the dropwise addition was completed, the temperature was slowly raised to room temperature, stirred at room temperature for 4 hours, and the raw material 1-(4-chlorophenyl The content of )-2-cyclopropyl-1-propanone is less than 1%, and 1.2 mol of water is added to the reaction system to quench the reaction after the reaction is completed. Distilled under reduced pressure to obtain 20 g of 1-(4-chlorophenyl)-2-cyclopropyl-1-propene A with a yield of 97.2%.

[0066] 2) Synthesis of epoxidized intermediate B

[0067] 1-(4-chlorophenyl)-2-cyclopropyl-1-propene A (20.6g, 100mmol), catalytic amount of titanium trichloride (5×10 -4 mol) and 2,3-naphthyridine ligand (5×10 -4 mol)...

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Abstract

The invention provides a method for synthesizing chiral cyproconazole, which comprises the following steps: carrying out ylide reaction on 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone used as the raw material and methylidene triphenyl phosphorane to generate 1-(4-chlorphenyl)-2-cyclopropyl-1-propylene; carrying out epoxidation reaction on the 1-(4-chlorphenyl)-2-cyclopropyl-1-propylene and an epoxidation reagent under the action of a transition metal catalyst to produce an epoxidation intermediate; and carrying out ring opening on the epoxidation intermediate and 1,2,4-triazole to obtain the target product chiral cyproconazole. The chiral cyproconazole synthesized by the method of the invention has the advantages of high optical purity (e.e% is greater than 80%) and high total reaction yield (greater than 75%), and is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis process of the pesticide cyclaconazole, in particular to a new method for synthesizing chiral cyclaconazole. Background technique [0002] Optically active pesticides are currently one of the most active research fields in pesticide chemistry in the world. According to the latest statistics, 28% of the commercialized agricultural chemicals are chiral compounds. Among the more than 170 kinds of chiral pesticides that have been commercialized, there are more than 30 kinds with annual sales exceeding US$100 million, and more than 60 kinds with annual sales exceeding US$25 million. Among them, chiral pesticides containing highly active chiral isomers The sales volume exceeds 10 billion US dollars, and the annual sales of chiral pesticides with pure optically active isomers is close to 3 billion US dollars. Chiral pesticides account for 35% of the global pesticide market. [0003] From the perspective of biological act...

Claims

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Application Information

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IPC IPC(8): C07D249/08C07B53/00A01P3/00
Inventor 刘迎春高源
Owner 合肥华纳生物医药科技有限公司
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