WO2023197384A1 - 一种铜催化一锅法制备大麻酚的方法 - Google Patents

一种铜催化一锅法制备大麻酚的方法 Download PDF

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WO2023197384A1
WO2023197384A1 PCT/CN2022/091072 CN2022091072W WO2023197384A1 WO 2023197384 A1 WO2023197384 A1 WO 2023197384A1 CN 2022091072 W CN2022091072 W CN 2022091072W WO 2023197384 A1 WO2023197384 A1 WO 2023197384A1
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preparation
cannabidiol
cbn
reaction
copper
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PCT/CN2022/091072
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王圣克
赵华
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上海锐康生物技术研发有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Definitions

  • the invention belongs to the field of chemical synthesis, and specifically relates to a copper-catalyzed one-pot method for preparing cannabidiol.
  • cannabidiol In addition to cannabidiol, cannabidiol (CBD) also exhibits many pharmacological activities, and there are related reports on its efficacy in epilepsy, depression and other diseases (Xu Wen, Zhang Jingjun. Research progress of cannabidiol in the treatment of epilepsy [J]. Shandong No. Journal of First Medical University (Shandong Academy of Medical Sciences), 2022, 43(01): 74-77; Huang Shuyun, et al. The role of cannabidiol in depression [J]. Chemistry of Life, 2021, 41(10): 2191-2195.).
  • THC tetrahydrocannabinol
  • CBD cannabidiol
  • CBN cannabidiol
  • organic synthesis strategies for fully synthetic or semi-synthetic CBN have been reported one after another, mainly involving the following strategies: 1. Intermolecular aromatic nucleophilic substitution to construct benzopyrans Ketone basic skeleton and subsequent methylation (Bull. Chem. Soc. Jpn. 1993, 66, 3034-3040; Adv. Synth. Catal. 2014, 356, 1337-1342); 2. Intramolecular cyclization reaction to construct benzene pyrone basic skeleton and subsequent methylation (Org. Lett. 2013, 15, 2574-2577); 3. Decarboxylation of cannabinolic acid (Planta Med.
  • the object of the present invention is to provide a method for preparing high-purity cannabinol (CBN) that is simple, efficient, low-cost, and has the potential for commercial large-scale production.
  • CBN cannabinol
  • the invention provides a preparation method of cannabidiol, which includes the following steps:
  • cannabidiol represented by formula I as raw material, reacting in a solvent under the action of reaction reagents: copper catalyst and oxidant, to obtain cannabidiol represented by formula II;
  • the above-mentioned copper catalyst is any one or more of CuCl 2 , CuBr 2 , Cu(OAc) 2 , CuCl, CuBr, and CuI;
  • the oxidizing agent is one or more of oxygen, iodophenylacetic acid, hydrogen peroxide, and dichlorodicyanobenzoquinone;
  • the solvent is any one or more of toluene, xylene, acetonitrile, N,N-dimethylformamide, tetrahydrofuran, and dimethyl sulfoxide.
  • the above-mentioned copper catalyst is CuBr 2 , Cu(OAc) 2 , CuCl or CuBr.
  • the molar ratio of the above-mentioned cannabidiol, copper catalyst and oxidizing agent is 1:(0.01 ⁇ 0.2):(0.5 ⁇ 5.0), preferably 1:(0.05 ⁇ 0.2):(3.0 ⁇ 5.0).
  • reaction reagents also include a catalyst ligand.
  • the catalyst ligand is p-toluenesulfonic acid.
  • the molar ratio of the above-mentioned cannabidiol and the catalyst ligand is 1: (0.5-2.5), preferably 1: (0.8-2.0).
  • reaction temperature is 0 to 120°C.
  • reaction temperature is 40 to 120°C.
  • reaction time is 2 to 48 hours.
  • reaction time is 6 to 48 hours.
  • This invention reports for the first time a new strategy for synthesizing CBN using copper as a catalyst, which is low-cost.
  • the product yield of the present invention is high (higher than 80%).
  • the method of the present invention can prepare CBN in one pot, is simple to operate, has mild reaction conditions, and is convenient for product separation and purification. It has good application prospects and promising economic benefits.
  • the raw materials and equipment used in the present invention are all known products and are obtained by purchasing commercially available products.
  • CBD 1.0mmol
  • p-toluenesulfonic acid 0.5mmol
  • Cu(OAc) 2 0.05mmol
  • dichlorodicyanobenzoquinone 3.0mmol
  • CBD 1.0mmol
  • Cu(OAc) 2 0.1mmol
  • iodophenylene diacetic acid 4.0mmol
  • TLC detects that the raw material reaction is complete.
  • saturated ammonium chloride to quench, extract, dry, rotary evaporate, and separate and purify by column chromatography to obtain CBN with a yield of 84%.
  • CBD (1.0mmol), CuBr 2 (0.1mmol), and hydrogen peroxide (3.0mmol) into a one-neck flask and dissolve in acetonitrile (5mL). The temperature is raised to 80°C and reacted for 48 hours. Add saturated ammonium chloride to quench, extract, dry, Separate and purify by rotary evaporation and column chromatography to obtain CBN with a yield of 72%.
  • CBD 1.0mmol
  • Cu(OAc) 2 0.2mmol
  • dichlorodicyanobenzoquinone 5.0mmol
  • THF 5mL
  • the temperature is raised to 100°C and reacted for 24 hours.
  • the raw materials are detected by TLC.
  • saturated ammonium chloride is added to quench it, followed by extraction, drying, rotary evaporation, and column chromatography separation and purification to obtain CBN with a yield of 83%.
  • CBD 1.0mmol
  • p-toluenesulfonic acid 0.8mmol
  • CuCl 2 0.2mmol
  • toluene 5mL
  • oxygen 4 to 5 times the equivalent of CBD
  • TLC detects that the raw material reaction is complete.
  • saturated ammonium chloride to quench, extract, dry, rotary evaporate, and column chromatography for separation and purification. , CBN was obtained with a yield of 75%.
  • CBD 1.0mmol
  • p-toluenesulfonic acid 2mmol
  • CuI 0.2mmol
  • a three-way glass valve to fill the reaction flask with normal pressure oxygen (according to The volume of the flask, oxygen is 4 to 5 times the equivalent of CBD), raise the temperature to 60°C and react for 24 hours.
  • TLC detects that the raw material reaction is complete.
  • Add saturated ammonium chloride to quench, extract, dry, rotary evaporate, and column chromatography to separate and purify. Obtain CBN, yield 84%.
  • CBD 1.0mmol
  • CuBr 0.2mmol
  • THF trifluorofuran
  • the oxygen is 4% of CBD ⁇ 5 times equivalent
  • add saturated ammonium chloride to quench, extract, dry, rotary evaporate, and separate and purify by column chromatography to obtain CBN with a yield of 88%.
  • CBD 1.0mmol
  • CuCl 0.2mmol
  • dichlorodicyanobenzoquinone 4.0mmol
  • CBD 1.0mmol
  • p-toluenesulfonic acid 2.0mmol
  • Cu(OAc) 2 0.2mmol
  • dichlorodicyanobenzoquinone 5.0mmol
  • TLC detects that the reaction of the raw materials is complete.
  • Add saturated ammonium chloride to quench, extract, dry, rotary evaporate, and separate and purify by column chromatography to obtain CBN with a yield of 78%.
  • the present invention reports for the first time a new strategy for the synthesis of CBN using copper as a catalyst.
  • Cannabidiol can be prepared through a one-pot reaction using cannabidiol as a raw material. It is simple, efficient, low-cost, and has the potential for commercial large-scale production.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

提供了以铜作为催化剂合成CBN的新方法，以大麻二酚为原料，在溶剂中，铜催化剂和氧化剂作用下反应，即可制得大麻酚；所述方法是一锅法反应，简单高效、成本低廉，具有商业化大规模生产大麻酚的潜力。

Description

一种铜催化一锅法制备大麻酚的方法 技术领域
本发明属于化学合成领域，具体涉及一种铜催化一锅法制备大麻酚的方法。
背景技术
众所周知，医用大麻对人类有诸多医疗益处，其根本原因是人类体内存在着调节各个生理系统的总指挥——内源性大麻素系统(Nature 1993,365,61–65；J.Med.Chem.2005,48,7166–7171)。Anu Mahadevan和Atmaram D.等人研究发现，大麻酚(CBN)及其衍生物可以选择性地与人体受体作用，具有高效的抗菌、镇静等作用(J.Med.Chem.2000,43,3778-3785)。除大麻酚外，大麻二酚(CBD)也展现出诸多药理活性，对癫痫、抑郁症等疾病的疗效也有相关报道(徐雯,张敬军.大麻二酚治疗癫痫的研究进展[J].山东第一医科大学(山东省医学科学院)学报,2022,43(01):74-77；黄淑芸,等.大麻二酚在抑郁症中的作用[J].生命的化学,2021,41(10):2191-2195.)。然而，尽管大麻二酚(CBD)不存在致幻作用，但在后续转化中存在生成四氢大麻酚(THC)的可能，而THC是大麻中的主要精神活性物质，被列入第一类精神药品品种目录管制。
因此，若能对大麻二酚(CBD)进行进一步转化，以规避使用过程中产生四氢大麻酚(THC)的可能，同时合成更高附加值的，具备不同于CBD医药用途的大麻酚(CBN)，将有利于进一步拓宽CBD和CBN的价值。
目前，由于大麻酚(CBN)具有重要的潜在医用价值，关于全合成或半合成CBN的有机合成策略相继被报道，主要涉及以下几种策略：1.分子间芳香亲核取代构建苯并吡喃酮基本骨架并进行后续甲基化(Bull.Chem.Soc.Jpn.1993,66,3034-3040；Adv.Synth.Catal.2014,356,1337–1342)；2.分子内环化反应构筑苯并吡喃酮基本骨架并进行后续甲基化(Org.Lett.2013,15,2574-2577)；3.大麻酚酸脱羧基(Planta Med.2007,73,273-275)；4.由[2+2+2]环加成反应构筑(Org.Lett.2008,10,2195-2198)；5.通过大麻二酚(CBD)的衍生化反应(J.Nat.Prod,2018,81,630-633；Free Radical Bio.Med.2021,164,258-270、专利申请WO2020031179(A1))。
然而，目前CBN的合成方法中，全合成步骤繁琐；而由大麻二酚(CBD)合成大麻酚(CBN)的策略通常需要添加计量(大过量)的碘单质来促进反应。因此，目前已知的大麻酚(CBN)的合成方法由于流程复杂、成本高等原因尚未见商业化生产，因此，亟需开发一种简单高效、成本低廉，具有商业化大规模生产潜力的制备高纯度大麻酚(CBN)的方法，以满足市场对于CBN的需求。
发明内容
本发明的目的在于提供一种简单高效、成本低廉，具有商业化大规模生产潜力的制备高纯度大麻酚(CBN)的方法。
本发明提供了一种大麻酚的制备方法，包括如下步骤：
以式I所示大麻二酚为原料，在反应试剂：铜催化剂、氧化剂作用下，于溶剂中反应，得到式II所示大麻酚；
反应式如下：
Figure PCTCN2022091072-appb-000001
进一步地，上述铜催化剂为CuCl 2、CuBr 2、Cu(OAc) 2、CuCl、CuBr、CuI中的任意一种或多种；
和/或，所述氧化剂为氧气、碘苯二乙酸、双氧水、二氯二氰基苯醌中的一种或多种；
和/或，所述的溶剂为甲苯、二甲苯、乙腈、N,N-二甲基甲酰胺、四氢呋喃、二甲基亚砜中的任意一种或多种。
更进一步地，上述铜催化剂为CuBr 2、Cu(OAc) 2、CuCl或CuBr。
进一步地，上述大麻二酚、铜催化剂和氧化剂的摩尔比为1:(0.01～0.2):(0.5～5.0)，优选为1:(0.05～0.2):(3.0～5.0)。
更进一步地，上述反应试剂还包括催化剂配体，优选地，所述催化剂配体为对甲苯磺酸。
更进一步地，上述大麻二酚和催化剂配体的摩尔比为1:(0.5～2.5)，优选为1:(0.8～2.0)。
进一步地，上述反应温度为0～120℃。
更进一步地，上述反应温度为40～120℃。
进一步地，上述反应时间为2～48h。
更进一步地，上述反应时间为6～48h。
本发明具有以下有益效果：
(1)本发明首次报道以铜作为催化剂合成CBN的新策略，成本低廉。
(2)本发明产物收率高(高于80％)。
(3)本发明的方法可一锅法制备CBN，操作简便，反应条件温和，产物分离提纯方便，具有良好的应用前景和可期的经济效益。
显然，根据本发明的上述内容，按照本领域的普通技术知识和惯用手段，在不脱离本发明上述基本技术思想前提下，还可以做出其它多种形式的修改、替换或变更。
以下通过实施例形式的具体实施方式，对本发明的上述内容再作进一步的详细说明。但不应将此理解为本发明上述主题的范围仅限于以下的实例。 凡基于本发明上述内容所实现的技术均属于本发明的范围。
具体实施方式
本发明所用原料与设备均为已知产品，通过购买市售产品所得。
实施例1、本发明方法制备CBN
将CBD(1.0mmol)、对甲苯磺酸(0.5mmol)、Cu(OAc) 2(0.05mmol)、二氯二氰基苯醌(3.0mmol)加入单口烧瓶中溶于甲苯(5mL)，升温至100℃反应24小时，TLC检测，加饱和氯化铵淬灭，萃取、干燥、旋蒸，柱层析分离纯化，得到CBN，收率86％。
实施例2、本发明方法制备CBN
将CBD(1.0mmol)、Cu(OAc) 2(0.1mmol)、碘苯二乙酸(4.0mmol)加入单口烧瓶中溶于二甲苯(5mL)，升温至120℃反应24小时，TLC检测原料反应完全，加饱和氯化铵淬灭，萃取、干燥、旋蒸、柱层析分离纯化，得到CBN，收率84％。
实施例3、本发明方法制备CBN
将CBD(1.0mmol)、CuBr 2(0.1mmol)、双氧水(3.0mmol)加入单口烧瓶中溶于乙腈(5mL)，升温至80℃反应48小时，加饱和氯化铵淬灭，萃取、干燥、旋蒸、柱层析分离纯化，得到CBN，收率72％。
实施例4、本发明方法制备CBN
将CBD(1.0mmol)、Cu(OAc) 2(0.2mmol)、二氯二氰基苯醌(5.0mmol)加入单口烧瓶中溶于THF(5mL)，升温至100℃反应24小时，TLC检测原料反应完全，加饱和氯化铵淬灭，萃取、干燥、旋蒸、柱层析分离纯化，得到CBN，收率83％。
实施例5、本发明方法制备CBN
将CBD(1.0mmol)、对甲苯磺酸(0.8mmol)、CuCl 2(0.2mmol)、溶于甲苯(5mL)加入三口烧瓶(25mL)中，利用三通玻璃阀使反应瓶中充满常压氧气(根据烧瓶容积，氧气为CBD的4～5倍当量)，升温至40℃反应48小时，TLC检测原料反应完全，加饱和氯化铵淬灭，萃取、干燥、旋蒸、柱层析分离纯化，得到CBN，收率75％。
实施例6、本发明方法制备CBN
将CBD(1.0mmol)、CuCl(0.2mmol)、二氯二氰基苯醌(4.0mmol)加入单口烧瓶中溶于DMSO(3mL)，升温至100℃反应36小时，TLC检测原料反应完全，加饱和氯化铵淬灭，萃取、干燥、旋蒸、柱层析分离纯化，得到CBN，收率85％。
实施例7、本发明方法制备CBN
将CBD(1.0mmol)、对甲苯磺酸(2mmol)、CuI(0.2mmol)、溶于DMF(3mL)加入三口烧瓶(25mL)中，利用三通玻璃阀使反应瓶中充满常压氧气(根据烧瓶容积，氧气为CBD的4～5倍当量)，升温至60℃反应24小时，TLC检测原料反应完全，加饱和氯化铵淬灭，萃取、干燥、旋蒸、 柱层析分离纯化，得到CBN，收率84％。
实施例8、本发明方法制备CBN
将CBD(1.0mmol)、CuBr(0.2mmol)、溶于THF(5mL)加入三口烧瓶(25mL)中，利用三通玻璃阀使反应瓶中充满常压氧气(根据烧瓶容积，氧气为CBD的4～5倍当量)，升温至90℃反应6小时，加饱和氯化铵淬灭，萃取、干燥、旋蒸、柱层析分离纯化，得到CBN，收率88％。
实施例9、本发明方法制备CBN
将CBD(1.0mmol)、CuCl(0.2mmol)、二氯二氰基苯醌(4.0mmol)加入单口烧瓶中溶于二甲苯(5mL)，升温至100℃反应36小时，TLC检测原料反应完全，加饱和氯化铵淬灭，萃取、干燥、旋蒸、柱层析分离纯化，得到CBN，收率81％。
实施例10、本发明方法制备CBN
将CBD(1.0mmol)、对甲苯磺酸(2.0mmol)、Cu(OAc) 2(0.2mmol)、二氯二氰基苯醌(5.0mmol)加入单口烧瓶中溶于乙腈(5mL)，升温至70℃反应12小时，TLC检测原料反应完全，加饱和氯化铵淬灭，萃取、干燥、旋蒸、柱层析分离纯化，得到CBN，收率78％。
产物CBN： 1H NMR(400MHz,CDCl 3)δ(ppm)8.16(dd,J＝1.1,0.5Hz,1H),7.14(d,J＝7.9Hz,1H),7.06(ddd,J＝7.9,1.7,0.6Hz,1H),6.43(d,J＝1.6Hz,1H),6.27(d,J＝1.6Hz,1H),5.31(s,1H),2.48(t,J＝7.9Hz,2H),2.38(s,3H),1.64–1.55(m,8H),1.36–1.27(m,4H),0.88(t,J＝6.9Hz,3H).
综上，本发明首次报道以铜作为催化剂合成CBN的新策略，以大麻二酚为原料，通过一锅法反应即可制备得到大麻酚，简单高效、成本低廉，具有商业化大规模生产潜力。

Claims (10)

  1. 一种大麻酚的制备方法，其特征在于，包括如下步骤：
    以式I所示大麻二酚为原料，在反应试剂：铜催化剂、氧化剂作用下，于溶剂中反应，得到式II所示大麻酚；
    反应式如下：
    Figure PCTCN2022091072-appb-100001
  2. 如权利要求1所述的制备方法，其特征在于，所述铜催化剂为CuCl 2、CuBr 2、Cu(OAc) 2、CuCl、CuBr、CuI中的任意一种或多种；
    和/或，所述氧化剂为氧气、碘苯二乙酸、双氧水、二氯二氰基苯醌中的一种或多种；
    和/或，所述的溶剂为甲苯、二甲苯、乙腈、N,N-二甲基甲酰胺、四氢呋喃、二甲基亚砜中的任意一种或多种。
  3. 如权利要求2所述的制备方法，其特征在于，所述铜催化剂为CuBr 2、Cu(OAc) 2、CuCl或CuBr。
  4. 如权利要求1所述的制备方法，其特征在于，所述大麻二酚、铜催化剂和氧化剂的摩尔比为1:(0.01～0.2):(0.5～5.0)，优选为1:(0.05～0.2):(3.0～5.0)。
  5. 如权利要求1～4任一项所述的制备方法，其特征在于，所述反应试剂还包括催化剂配体，优选地，所述催化剂配体为对甲苯磺酸。
  6. 如权利要求5所述的制备方法，其特征在于，所述大麻二酚和催化剂配体的摩尔比为1:(0.5～2.5)，优选为1:(0.8～2.0)。
  7. 如权利要求1所述的制备方法，其特征在于，所述反应温度为0～120℃。
  8. 如权利要求7所述的制备方法，其特征在于，所述反应温度为40～120℃。
  9. 如权利要求1所述的制备方法，其特征在于，所述反应时间为2～48h。
  10. 如权利要求9所述的制备方法，其特征在于，所述反应时间为6～48h。
PCT/CN2022/091072 2022-04-15 2022-05-06 一种铜催化一锅法制备大麻酚的方法 WO2023197384A1 (zh)

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WO2020031179A1 (en) * 2018-08-06 2020-02-13 Beetlebung Pharma Ltd. Methods for synthesis of cannabinoid compounds
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