Synthetic method of cannabidiol

A technology for cannabidiol and a synthesis method, which is applied in the directions of organic chemistry methods, chemical instruments and methods, active ingredients of hydroxyl compounds, etc., can solve problems such as large limitations in industrialized production, cumbersome steps, etc., and achieves good industrial application prospects and process improvement. , the effect of low price

Pending Publication Date: 2020-10-30
云南自由贸易试验区睿之成医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In addition to the above two chemical synthesis methods, there are some reports in the literature that cannabidiol is obtained by

Method used

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  • Synthetic method of cannabidiol
  • Synthetic method of cannabidiol
  • Synthetic method of cannabidiol

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0045] Example one

[0046] Preparation of Intermediate One:

[0047] Add 100g of 2,4-dimethoxy-6-pentylbenzoic acid methyl ester and 800mL of dichloromethane into a 2000mL three-necked flask, add 50ml of boron trifluoride ether with stirring, stir for 0.5 hour at 25°C, add dropwise 50g of (1S,4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexen-1-ol, after the dripping is completed, keep the mixture and stir for 24h. Cool the reaction solution to below 10°C, adjust the pH to 2~3 with 1N aqueous hydrochloric acid, add n-heptane (500mL×2) for extraction, adjust the pH to 10 with aqueous sodium carbonate solid, add n-heptane (500mL×2) Extract, wash with water (300 mL) once, dry with anhydrous sodium sulfate, and concentrate to dryness under reduced pressure to obtain a crude product. The crude product was dissolved by heating at 40°C with 4v / m n-heptane, cooling to -5~5°C for 16 hours, suction filtration, and drying to obtain 81g of white solid with a yield of 73% and an HPLC purity of 99.9...

Example Embodiment

[0052] Example two

[0053] Preparation of Intermediate One:

[0054] Add 100g of 2,4-dimethoxy-6-pentylbenzoic acid methyl ester and 300ml of DMF into a 1000ml three-necked flask, add 40ml of boron trifluoride ether with stirring, stir for 0.5 hour at 25°C, add 70g of (1S,4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexen-1-ol, after the addition is complete, keep it warm and stir for 15h. Cool the reaction solution to below 0℃, adjust the pH to 2~3 with 1N dilute sulfuric acid aqueous solution, add n-heptane (500mL×2) for extraction, adjust the pH to 10 with aqueous sodium carbonate solid, add n-heptane (500mL×3) ) Extraction, washing with water (300 mL); twice, drying with anhydrous sodium sulfate, and concentrating to dryness under reduced pressure to obtain a crude product. The crude product was dissolved by adding 4v / m n-heptane at 40°C, cooling to -5°C to 5°C for 16 hours, vacuum filtration, and drying to obtain 75g of white solid with a yield of 67% and an HPLC purity of 99.91%....

Example Embodiment

[0059] Example three

[0060] Preparation of Intermediate One:

[0061] Add 100g of 2,4-dimethoxy-6-pentylbenzoic acid methyl ester and 500mL of tetrahydrofuran into a 2000mL three-necked flask, add 50ml of boron trifluoride ether with stirring, stir for 0.5 hour at 25°C, add 70g of (1S,4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexen-1-ol, after the addition is complete, keep the mixture and stir for 18h. Cool the reaction solution to below 10°C, adjust the pH to 2~3 with glacial acetic acid, add n-heptane (500mL×2) for extraction, adjust the pH to 10 with aqueous sodium carbonate solid, add n-heptane (500mL×3) for extraction , Washed with water (300 mL) twice, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to dryness to obtain a crude product. The crude product was dissolved by heating at 40°C with 4v / m n-heptane, cooled to -5~5°C for 16 hours, suction filtered, and dried to obtain 79g of white solid with a yield of 71% and an HPLC purity of 99.92%.

[0...

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Abstract

The invention belongs to the field of chemical pharmacy, and particularly discloses a synthetic method of cannabidiol. The synthetic method comprises the following steps: S1, adopting 2, 4-dimethoxy-6-amyl methyl benzoate as a raw material, and carrying out a coupling reaction on the raw material and (1S, 4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexene-1-ol under a Lewis acid catalysis condition to obtain an intermediate (I); S2, performing high-temperature decarboxylation on the prepared intermediate (I) under the action of strong alkali to prepare an intermediate (II); and S3, removing methyl from the prepared intermediate (II) under the action of boron tribromide to obtain the final product cannabidiol. The purity of the cannabidiol obtained by the preparation method disclosed by the invention is 99.90-99.99%; the total yield of the finally prepared bulk drug with qualified purity can reach 60-80% at most, the process is obviously improved, and the method has a good industrial application prospect.

Description

technical field [0001] The invention belongs to the field of chemical pharmacy, and in particular relates to a synthesis method of cannabidiol. Background technique [0002] Cannabis has been used in traditional medicine for thousands of years and was first introduced to Western medicine in the 1830s. The original uses were analgesic, sedative, anti-inflammatory, antispasmodic and anticonvulsant effects. More than 100 years later, due to concerns about its safety, cannabis moved from being classified as a drug used in medical treatment to a narcotic, and was classified as a Schedule I drug in the US until 1970, meaning it was not accepted medical use. [0003] The alias of cannabidiol is L-trans-cannabidiol, and its English name is (-)-Cannabidiol. It is a very marketable raw material drug. The structural formula of the compound is: [0004] [0005] At present, cannabidiol is mainly used for nerve protection, anti-spasm, anti-inflammatory and anti-anxiety effects. In...

Claims

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Application Information

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IPC IPC(8): C07C39/23C07C37/055A61K31/05A61P25/08A61P19/02A61P29/00A61P35/00A61P25/20A23L33/105
CPCC07C39/23C07C37/055C07C41/18C07C67/343A61P25/08A61P19/02A61P29/00A61P35/00A61P25/20A23L33/105C07C2601/16C07B2200/07C07B2200/09A23V2002/00C07C43/215C07C69/92A23V2200/322A23V2200/308A23V2200/30A23V2250/2132
Inventor 朱常成席亮尹子丽金毅廖荣李之恒甘昌敏杨金芳谢富兰
Owner 云南自由贸易试验区睿之成医药科技有限公司
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