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Method for continuously preparing cannabidiol intermediate through green photooxidation

A technology of cannabidiol and a synthesis method, which is applied in chemical instruments and methods, preparation of hydroxyl compounds, preparation of organic compounds, etc., can solve the problem of high comprehensive process cost, and achieve the effects of relatively low cost, environmental friendliness, and effective synthesis methods.

Pending Publication Date: 2021-07-30
ZHEJIANG JIUZHOU PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the synthesis steps, diphenyl diselenide, sodium borohydride, and hydrogen peroxide, which are dangerous reagents, are also used. The last step also uses high-temperature operation, and the overall process cost is relatively high.

Method used

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  • Method for continuously preparing cannabidiol intermediate through green photooxidation
  • Method for continuously preparing cannabidiol intermediate through green photooxidation
  • Method for continuously preparing cannabidiol intermediate through green photooxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]Add (R)-(+)-limonene (6.80g, 49.92mmol, 1.0eq), acetonitrile (180mL, 26.5V) and catalyst (126mg, 0.12mmol) sequentially into a 250mL glass one-necked bottle, and stir to dissolve. The reaction solution was pumped into the photochemical reactor using a convective pump, and oxygen was continuously fed in at the same time, irradiated continuously with a tungsten halogen lamp (250W) for 18 hours, sampling was controlled, and the residual raw material was 6.9% (GC, area%). The reaction solution was concentrated under reduced pressure to 100 mL, and an aqueous solution of sodium sulfite (12.58 g, 2.0 eq, 15%) was slowly added under ice-cooling, and stirred while adding. After the dropwise addition, a large amount of solid precipitated out. Remove the ice-water bath, continue to stir at room temperature for 2 hours, then raise the temperature to reflux, and keep stirring for 2 hours. Cool down to 40-50°C and concentrate under reduced pressure to remove acetonitrile, add water ...

Embodiment 2

[0041] Add (R)-(+)-limonene (6.80g, 49.92mmol, 1.0eq), acetonitrile (200mL, 29.4V) and catalyst (126mg, 0.12mmol) sequentially into a 250mL glass one-necked bottle, and stir to dissolve. The reaction solution was pumped into the photochemical reactor using a parallel flow pump, and oxygen was continuously fed in at the same time, and the tungsten halogen lamp (500W) was continuously irradiated for 20 hours, and the sampling was controlled, and the residual raw material was 4.2% (GC, area%). The reaction solution was concentrated under reduced pressure to 100 mL, and an aqueous solution of sodium sulfite (12.58 g, 2.0 eq, 15%) was slowly added under ice-cooling, and stirred while adding. After the dropwise addition, a large amount of solid precipitated out. Remove the ice-water bath, continue to stir at room temperature for 2 hours, then raise the temperature to reflux, and keep stirring for 2 hours. Cool down to 40-50°C and concentrate under reduced pressure to remove acetoni...

Embodiment 3

[0043] Add (R)-(+)-limonene (3.40g, 24.96mmol, 1.0eq), acetonitrile (700mL, 205V) and catalyst (63mg, 0.06mmol) to a 1000mL glass one-necked flask in sequence, and stir to dissolve. The reaction solution was pumped into the photochemical reactor using a convection pump, and oxygen was continuously fed in at the same time, irradiated continuously with a tungsten halogen lamp (500W) for 36 hours, the sampling was controlled, and the residual raw material was 8.2% (GC, area%). The reaction solution was concentrated under reduced pressure to 100 mL, and an aqueous solution of sodium sulfite (12.58 g, 2.0 eq, 15%) was slowly added under ice-cooling, and stirred while adding. After the dropwise addition, a large amount of solid precipitated out. Remove the ice-water bath, continue to stir at room temperature for 2 hours, then raise the temperature to reflux, and keep stirring for 2 hours. Cool down to 40-50°C and concentrate under reduced pressure to remove acetonitrile, add water ...

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Abstract

The invention relates to a novel method for synthesizing cannabidiol (-)-Cannabidiol (CBD, formula I), aiming at solving the defects in the prior art. The production process is characterized by comprising the following steps that: (R)-(+)-Limonene (compound I-a) is adopted as an initial raw material; the initial raw material and a photocatalyst are subjected to an oxidation reaction under illumination,and then a reduction reaction is performed; and a pure key intermediate I-e is obtained through purification. The reaction formula involved in the steps is shown in the specification. The reaction and purification are simple; The method of the invention has the advantages of simple and easy-to-implement technical route, wide raw material source range, mild conditions, low production cost, high yield and environment-friendly performance, and provides a more effective synthesis method for industrial production.

Description

technical field [0001] The present invention relates to the technical field of drug synthesis. Specifically, the present invention relates to a new method for synthesizing cannabidiol (Formula I). ​​The technology adopted in the present invention has the advantages of simple and easy route, mild conditions and low production cost. Background technique [0002] (-)-Cannabidiol (CBD, formula I) is a natural extract of the major non-psychotic constituents of the cannabis plant, which has diverse pharmacological effects, including anxiolytic, antipsychotic, antiemetic, and anti-inflammatory properties. Although cannabidiol has low affinity for cannabinoid CB1 and CB2 receptors, it is a potent GPR55 antagonist. In June 2018, Epidiolex, an oral cannabidiol solution, received FDA approval for the treatment of patients 2 years and older with a rare form of epilepsy: Lennox–Gastaut syndrome or Dravet syndrome. The drug is developed and manufactured by GW Pharmaceuticals in the UK. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/00C07C35/17
CPCC07C29/00C07C35/17
Inventor 王郁萱李智温进富姚志刚邵军超蒋志强张镇宋亮郑辉高照波梅义将
Owner ZHEJIANG JIUZHOU PHARM CO LTD
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