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Preparation method of progesterone

A progesterone and reaction technology, applied in the directions of organic chemistry, steroids, organic chemistry, etc., can solve the problems of heavy metal ions, uneconomical atoms, cumbersome processes, etc., to improve the reaction yield, avoid high toxicity, and reduce the reaction high yield effect

Active Publication Date: 2019-05-21
SHANGHAI GONGTUO PHARMA & CHEM IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

From the known literature reports, the chemical synthesis route of progesterone using compound (2) still has problems such as cumbersome process, heavy metal ion pollution, atomic diseconomy, and low yield.

Method used

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  • Preparation method of progesterone
  • Preparation method of progesterone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation of Progesterone (1):

[0032] Compound (2) (16.53g; Fw: 330.50; 50mmol), methylene chloride 150mL, anhydrous copper acetate (0.091g) were added successively in a dry 250mL there-necked flask equipped with a thermometer, a reflux condenser and magnetic stirring and filled with nitrogen. ; Fw: 181.65; 0.5 mmol), NMP (0.050 g; Fw: 99.13; 0.5 mmol) TEMPO (0.078 g; Fw: 156.25; 0.5 mmol), N,N-dimethylaniline (0.061 g; Fw: 121.18; 0.5 mmol). The temperature of the system was then lowered to 0°C, and dry air was introduced. As the air was introduced into the system, the system gradually turned brown-red, and the temperature of the system was maintained at 0 °C during the air-introduction process. After feeding for about 12 hours, after the reaction was completed, 2M hydrochloric acid was slowly added dropwise to the reaction system, the pH was adjusted to neutrality, the organic phase was separated, the aqueous phase was extracted with dichloromethane, and then th...

Embodiment 2

[0034] Preparation of Progesterone (1):

[0035] Compound (2) (16.53g; Fw: 330.50; 50mmol), acetonitrile 150mL, anhydrous copper chloride (0.134g) were added successively in a dry nitrogen-filled 250mL there-necked flask equipped with a thermometer, reflux condenser, and magnetic stirring; Fw: 134.45; 1.0 mmol), NMP (0.10 g; Fw: 99.13; 1.0 mmol), TEMPO (0.16 g; Fw: 156.25; 1.0 mmol), N,N-dimethylaniline (0.12 g; Fw: 121.18; 1.0 mmol). The temperature of the system was then lowered to 0°C, and dry air was introduced. As the air was introduced into the system, the system gradually turned brown-red, and the temperature of the system was maintained at 0 °C during the air-introduction process. After feeding for about 12 hours, after the reaction was completed, 2M hydrochloric acid was slowly added dropwise to the reaction system, the pH was adjusted to neutrality, the organic phase was separated, the aqueous phase was extracted with dichloromethane, and then the organic phases we...

Embodiment 3

[0037] Preparation of Progesterone (1):

[0038] Compound (2) (16.53g; Fw: 330.50; 50mmol), acetonitrile 150mL, anhydrous copper fluoroborate (2.37g) were added successively in a dry nitrogen-filled 250mL there-necked flask equipped with a thermometer, reflux condenser, and magnetic stirring; Fw: 237.14; 10.0 mmol), NMP (1.00 g; Fw: 99.13; 10.0 mmol), TEMPO (1.56 g; Fw: 156.25; 10.0 mmol), N,N-dimethylaniline (1.21 g; Fw: 121.18; 10.0 mmol). The temperature of the system was then lowered to 0°C, and dry oxygen was introduced. With the introduction of oxygen into the system, the system gradually turned brown-red, and the system continued to exotherm during the introduction of oxygen, and the temperature of the system was maintained at 30 °C. After feeding for about 0.5h, after the reaction was completed, 2M hydrochloric acid was slowly added dropwise to the reaction system, the pH was adjusted to neutral, the organic phase was separated, the aqueous phase was extracted with d...

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Abstract

The invention discloses a preparation method of progesterone. The method comprises the following steps: introducing pure oxygen or air into a mixture composed of a compound (2), a copper catalyst, TEMPO, NMP, N,N-dialkylaniline and a solvent to perform reaction, and collecting the progesterone from the reaction product. The method avoids using the heavy metal agent, greatly increases the reaction yield, and greatly lowers the production cost. The progesterone prepared by the method has high stereoselectivity, and the purity can reach 99% or above after simple purification; and thus, the method is convenient for industrialized implementation. The reaction equation is disclosed in the specification.

Description

technical field [0001] The present invention relates to a new process for preparing progesterone. Background technique [0002] Progesterone, also known as progesterone, is the main biologically active progesterone secreted by the ovary. Progesterone can protect the endometrium of women. During pregnancy, progesterone hormones can provide support and protection for the early growth and development of the fetus, and can play a certain role in calming the uterus. In addition, the relationship between progesterone and estrogen is inseparable, both of which are very important female hormones. The role of estrogen is mainly to promote the development and maturity of female secondary sexual characteristics, while progesterone further promotes the development and maturity of secondary sexual characteristics on the basis of the role of estrogen, and there is a synergistic effect between the two. The structure is as follows: [0003] [0004] At present, the most classic synthe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J7/00
CPCC07B2200/07C07J7/002
Inventor 施彬建蒋青锋杨文棋杨坤
Owner SHANGHAI GONGTUO PHARMA & CHEM IND
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