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Preparation method of lysergol

A technology of lysergol and lysergic acid, applied in the field of medicine, can solve the problems of unfriendly environment, low yield of lysergol and the like

Active Publication Date: 2017-03-15
CHONGQING QIANTAI BIOLOGICAL MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] At present, the methods for preparing ergool reported in the existing literature are all realized by the reduction of methyl ergotate, which has various defects such as low yield of ergool and unfriendly environment.

Method used

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  • Preparation method of lysergol
  • Preparation method of lysergol
  • Preparation method of lysergol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1: slough the preparation of the lysergic acid of crystallization water

[0061] A mechanical stirrer, a thermometer, a reflux condenser and a nitrogen protection device were installed in a 2L three-necked flask. Add 50g of lysergic acid [purity 97.91%, content (calculated as anhydrous matter) 91.90%] 50g, methanol 1000g and ammonia water 25g into the three-necked bottle, stir to dissolve. Add 10 g of 819-type activated carbon and 100 g of anhydrous sodium sulfate, stir and heat up to reflux. Keep the temperature and stir for 1~2h, filter while it is hot, concentrate the mother liquor under reduced pressure to about 1 / 10 of the original volume, a large amount of solid precipitates, add 100g of methanol, beat at 20~30°C for 1~2h, filter, and filter the cake at 50~60 ℃ and dried under reduced pressure to obtain 35.28 g of lysergic acid with a purity of 99.14% (the HPLC spectrum is attached figure 1 shown), the content (calculated as anhydrous matter) is 98.16...

Embodiment 2

[0062] Embodiment 2: Lysergic acid prepares ergot alcohol

[0063] Install mechanical stirring, thermometer, reflux condenser, drying tube and nitrogen protection device in the 1L three-necked flask. Add 20 g of lysergic acid (purified) and 200 g of pre-dried tetrahydrofuran prepared in Example 1 into the three-necked flask. Stir and lower the temperature to 0~10°C, add 8.50g of lithium aluminum hydride in batches, after the addition, slowly raise the temperature to reflux reaction (reaction liquid temperature 60~70°C). Keep the temperature and stir for 24 hours. After the reaction is complete as monitored by TLC, the temperature is lowered to 0~10°C. Slowly add 200g of 10% ammonium chloride aqueous solution dropwise, after the dropwise addition is complete, continue stirring for 2~3h. Add 10 g of diatomaceous earth and continue stirring for 0.5~1h. Filter and wash the filter cake with tetrahydrofuran / water mixture (20g / 20g). Add 300g of ethyl acetate to the mother liquor,...

Embodiment 3

[0064] Embodiment 3: Lysergic acid prepares ergot alcohol

[0065] Add 2.11g of sodium borohydride and 50g of chloroform into a 250ml three-necked flask, add 5g of decrystallized lysergic acid (purified) prepared in Example 1 under stirring at room temperature, continue stirring for 0.5~1h after adding, slowly add iodine (7.10 g) in chloroform (20 g) solution. After dropping, the temperature was raised to reflux and stirred for 10~15h. After the completion of the reaction was monitored by TLC, the temperature was lowered to 0-10°C. Add 20 g of methanol dropwise, and continue stirring for 3 to 5 hours after the dropwise addition is complete. Add 2g of activated clay and continue stirring for 0.5~1h. Filter, wash the filter cake with chloroform / methanol mixture (15g / 5g), combine the mother liquor, add 30g of water, stir for 5-10min, and separate the liquids. The aqueous phase was extracted twice with chloroform / methanol mixture (30g / 10g). Combine the organic phases, concent...

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Abstract

The invention provides a preparation method of lysergol, and more specifically provides a method for preparing the lysergol directly through a one-step reduction reaction of lysergic acid. A solvent and a reagent adopted in the invention have the advantages of low toxicity, low cost, simple post-processing and the like, and can be recycled and reused; the preparation method is free of special requirement for equipment, and is short in operation working time and low in energy consumption.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a method for preparing ergodol, more specifically to a method for preparing ergodol by subjecting lysergic acid to a one-step reduction reaction. Background technique [0002] Nicergoline has a good therapeutic effect on vascular dementia, and ergot alcohol is a key intermediate for preparing nicergoline. Comprehensive literature reports, the preparation route of ergot alcohol has following two kinds. [0003] Synthetic Route 1: Hydrolyze the ergonovine obtained by biological fermentation under alkaline conditions to obtain lysergic acid. The alkaline conditions can be sodium hydroxide or potassium hydroxide aqueous solution, etc.; then methylate lysergic acid to obtain lysergic acid Methyl ester, the esterification condition can be methyl alcohol / concentrated sulfuric acid or methanol / hydrogen chloride etc.; Finally methyl lysergic acid is reduced to obtain ergot ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D457/00
CPCC07D457/00
Inventor 叶健张有理刘省伟吴禄春袁建栋
Owner CHONGQING QIANTAI BIOLOGICAL MEDICINE
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