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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 biological extraction, but the steps of such methods are relatively cumbersome, and the limitations of industrial production are too large

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

Embodiment 1

[0046] Preparation of intermediate one:

[0047] Add 100g of methyl 2,4-dimethoxy-6-pentylbenzoate and 800mL of dichloromethane into a 2000mL three-neck flask, add 50ml of boron trifluoride ether under stirring, stir at 25°C for 0.5 hours, drop 50g of (1S,4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexen-1-ol was added dropwise and kept stirring for 24 hours. Cool the reaction solution below 10°C, adjust the pH to 2-3 with 1N hydrochloric acid aqueous solution, add n-heptane (500mL×2) for extraction, adjust the pH to 10 with solid sodium carbonate in the aqueous phase, add n-heptane (500mL×2) Extracted, washed with water (300 mL) once, dried over anhydrous sodium sulfate, concentrated under reduced pressure to dryness to obtain a crude product. Add 4 v / m n-heptane to the crude product and heat to dissolve at 40°C, cool down to -5-5°C for 16 hours, keep warm and crystallize, filter with suction, and dry to obtain 81g of white solid with a yield of 73% and a purity of 99.96% by HPLC....

Embodiment 2

[0053] Preparation of intermediate one:

[0054] Add 100g of methyl 2,4-dimethoxy-6-pentylbenzoate and 300mL of DMF into a 1000mL three-necked flask, add 40ml of boron trifluoride ether under stirring, stir at 25°C for 0.5 hours, and dropwise add 70g of (1S,4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexen-1-ol, after the dropwise addition, keep stirring for 15 hours. Cool the reaction solution below 0°C, 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 solid sodium carbonate in the aqueous phase, add n-heptane (500mL×3 ) extraction, washed with water (300mL); twice, dried over anhydrous sodium sulfate, concentrated under reduced pressure to dryness to obtain a crude product. The crude product was dissolved by adding 4 v / m n-heptane at 40°C, cooled to -5-5°C for 16 hours, and then crystallized at -5°C for 16 hours. After suction filtration and drying, 75g of a white solid was obtained. The yield was...

Embodiment 3

[0060] Preparation of intermediate one:

[0061] Add 100g of methyl 2,4-dimethoxy-6-pentylbenzoate and 500mL of tetrahydrofuran into a 2000mL three-neck flask, add 50ml of boron trifluoride ether under stirring, stir at 25°C for 0.5 hours, and dropwise add 70g of (1S,4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexen-1-ol, after the dropwise addition, keep stirring for 18 hours. Cool the reaction solution 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 solid sodium carbonate in the aqueous phase, add n-heptane (500mL×3) for extraction , washed with water (300 mL) twice, dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure to obtain a crude product. Add 4 v / m n-heptane to the crude product and heat to dissolve at 40°C, cool down to -5-5°C for crystallization for 16 hours, filter with suction, and dry to obtain 79g of white solid with a yield of 71% and a purity of 99.92% by ...

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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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