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Preparation method of 17-formic acid steroid compound

A technology of steroidal compounds and compounds, applied in the field of preparation of 17-formic acid steroidal compounds, can solve the problems of low reaction temperature, unfriendly environment, increased production energy consumption, etc., and achieve mild reaction conditions and less alkali consumption , The effect of reducing the production of isomers

Active Publication Date: 2022-01-25
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] It is reported in the literature that NBS and dibromohydantoin are used as halogenation reagents for haloform reaction. Although the use of halogens is avoided, there is also a large reaction solvent ratio, and the solvent cannot be recovered. Applied mechanically, a large amount of wastewater containing dioxane is produced, which is not friendly to the environment and requires low reaction temperature, increases production energy consumption, low yield and low purity, etc.

Method used

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  • Preparation method of 17-formic acid steroid compound
  • Preparation method of 17-formic acid steroid compound
  • Preparation method of 17-formic acid steroid compound

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preparation example Construction

[0021] This specific embodiment proposes a preparation method of 17-formic acid steroid compound, which is characterized in that it comprises the following steps: dissolving compound 1 in an organic solvent, then adding a base, and then adding PyHBr 3 (i.e. pyridinium bromide salt) stirred at 20-30°C for 2-4h, continued to add sodium bisulfite to the reaction product to quench the reaction, then adjusted the pH to 2-3 with acid, and then distilled and recovered the organic solvent, followed by washing and drying to obtain the 17-formic acid steroid compound (ie compound 2); the structural formula of the compound 1 is The organic solvent is one or both of 1,4-dioxane and tetrahydrofuran; the alkali is one or more of sodium hydroxide, potassium hydroxide, sodium tert-butoxide and potassium tert-butoxide Kind; The compound 1 and the PyHBr 3 The mass ratio is (1-2):(1.5-3); the material ratio of the compound 1 to the organic solvent is 1g:10-20mL.

[0022] The reaction equation...

Embodiment 1

[0026] The present embodiment proposes a preparation method of 17-formic acid steroid compound, comprising the following steps: dissolving 5 g of compound 1 in 50 ml of 1,4-dioxane, adding 50 ml of 40% aqueous sodium hydroxide solution, and slowly adding in three times 7.5gPyHBr 3 , after stirring for 2 hours at 20°C, add 5ml of 15% sodium bisulfite to quench the reaction, adjust pH=2 with concentrated hydrochloric acid, recover 1,4-dioxane by atmospheric distillation, add 100ml of water, stir, filter, filter The cake was rinsed with water until it was neutral, and air-dried at 50°C to obtain compound 2 with a yield of 96.7%, a purity of 98.615%, and a recovery of 1,4-dioxane of 91.5%.

[0027] From figure 1 It can be seen that the 17-formic acid steroid compound was obtained with high purity.

Embodiment 2

[0029] The present embodiment proposes a kind of preparation method of 17-formic acid steroid compound, comprises the following steps:

[0030] Dissolve 20g of compound 1 in 200ml of 1,4-dioxane, add 200ml of 45% potassium hydroxide aqueous solution, and slowly add 30g of PyHBr in three 3 , after stirring for 2 hours at 30°C, add 20ml of 15% sodium bisulfite to quench the reaction, adjust the pH to 2 with concentrated hydrochloric acid, recover 1,4-dioxane by atmospheric distillation, add 400ml of water, stir, filter, filter The cake was rinsed with water until it was neutral, and air-dried at 50°C to obtain Compound 2 with a yield of 96.3%, a purity of 98.252%, and a recovery of 1,4-dioxane of 92.8%.

[0031] From figure 2 It can be seen that the 17-formic acid steroid compound was obtained with high purity.

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Abstract

The invention relates to a preparation method of a 17-formic acid steroid compound. The method comprises the following steps: dissolving a compound 1 in an organic solvent, then adding alkali, then adding PyHBr3, and carrying out a stirring reaction at 20-30 DEG C to obtain the 17-formic acid steroid compound, wherein the structural formula of the compound 1 is that the volume concentration of the alkali is 8.5%-45%, and the volume ratio of the compound 1 to the alkali is 1g: 10-15mL. The yield of the 17-formic acid steroid compound prepared by the preparation method provided by the invention is up to 95% or above, and the purity is up to 98% or above.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 17-formic acid steroid compound. Background technique [0002] 17-Formic acid steroids are a common and very important molecular intermediate of steroid hormone drugs. A series of products such as finasteride and dutasteride can be synthesized through 17-formic acid steroid compounds. In addition, some important steroid intermediates and drug molecules also have 17-formic acid or 17-formic acid derivative group structure, therefore, the synthesis of 17-formic acid steroid compounds is of great significance. [0003] The synthesis of traditional 17-formic acid compounds is the application of haloform reaction, using halogens (such as bromine, chlorine) as halogenating reagents, halogens have high, volatile, difficult to transport and store, pollute the environment and other shortcomings, in large-scale production There is a great security risk. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
CPCC07J7/002
Inventor 戴枫林谢来宾唐小海胡雄
Owner HUNAN KEREY BIOTECH
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