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Novel process for preparing progesterone

A new process, the technology of progesterone, is applied in the field of preparation of progesterone, which can solve the problems of low yield of extract, complex synthesis process, low efficiency of progesterone, etc., and achieve the effect of short process flow, low preparation cost and easy availability of raw materials

Inactive Publication Date: 2013-05-08
HUNAN KEYUAN BIO PRODS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] U.S. Patents US19850782068, US4780420A, US20060494425, US20080120959; US2008319204A1 disclose the synthesis method of progesterone. Their synthetic raw materials are all made of natural plant extracts as raw materials. The yield of natural product extracts is low and the cycle is long (because natural products need a growth cycle) , resulting in low efficiency in the production of progesterone. Chinese patent 201110007898.1 also discloses a synthetic method for progesterone. Its patent route is to adopt the synthetic route (1) mentioned above to synthesize, and its synthetic method is still to use natural products as synthetic raw materials. Dienolone acetate is synthesized, and progesterone is obtained from dienolone acetate through Raney nickel hydrogenation reduction, hydrolysis, and Woshi oxidation. The synthesis process is complicated, especially toluene must be completely anhydrous to react. Long time anhydrous treatment, aluminum isopropoxide can participate in the reaction, post-treatment requires water vapor flushing, high energy consumption, long processing time, especially if the water vapor is too high, lutein is taken out by water vapor, resulting in low yield , the water vapor is so open that the small cyclohexanone cannot be flushed out and the product cannot be precipitated. The uneven flushing will also cause some places to be solid and some places to be oily. It is difficult to control the best conditions for post-treatment.

Method used

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  • Novel process for preparing progesterone
  • Novel process for preparing progesterone
  • Novel process for preparing progesterone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] In a 500ml three-neck flask equipped with a thermometer and agitator, carefully add 30 grams of raw material 17α-hydroxyprogesterone and 210ml of anhydrous pyridine (pyridine is first anhydrous, otherwise it will form a salt with acid and no colorless liquid will be obtained) , after nitrogen replacement three times, carefully add 35ml of phosphorus oxychloride, and stir at room temperature for 10 minutes. At this time, the reaction solution is a light yellow transparent liquid. Slowly raise the temperature to 80°C, the color of the reaction solution gradually becomes darker, and finally turns into a brown reaction solution , continue to let it stir for 12 hours, after TLC detects that the reaction of the raw materials is complete, cool the reaction solution to about 40°C and pour the reaction solution into 1 liter of 3 mol / liter hydrochloric acid solution stirred at a high speed, let it stir for 15 minutes, filter, and use 5% Wash with sodium carbonate solution until ne...

Embodiment 2

[0039] A: Preparation of Raney nickel catalyst: In a 2000ml reaction bottle, add 350ml of water, add 38g of sodium hydroxide under stirring, heat up to 50°C after dissolving, add 25g of aluminum-nickel alloy (100-200 mesh) in batches, and the temperature of the feeding process Keep it at 50-55°C, raise the temperature to 70°C and stir for 1 hour after the addition, let stand, pour off the upper layer of water, then add 100ml of water and stir, then pour off the water, repeat this for 3 times, and then wash with ethanol for 3 times. To test the activity of the catalyst, the detection method is to put a small amount of the catalyst on the filter paper and let the ethanol evaporate to dryness, and then emit sparks to prove that the catalyst is active.

[0040] B: Add 25 grams of the eliminated product into a 500ml autoclave, add 180ml of ethanol, add two teaspoons of the Raney nickel catalyst prepared in the previous step, tighten the screw on the sealing cover, replace it with hi...

Embodiment 3

[0043] In a 500ml three-necked flask equipped with a thermometer and stirring, carefully add 30 grams of raw material 17α-hydroxyprogesterone and 200ml of DMF, add 5 grams of sodium azide, and stir at room temperature for 10 minutes. At this time, the reaction solution is a light yellow transparent liquid. Slowly raise the temperature to 50°C, the color of the reaction solution gradually becomes darker, and finally turns into a brown reaction solution. Continue to let it stir for 12 hours. After the reaction of the raw materials is detected by TLC, cool down and pass through the column to obtain 26 grams of the eliminated product. Yield: 86.7% .

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Abstract

The invention provides a novel process for preparing progesterone, and belongs to the technical field of organic synthesis. The novel process comprises the following steps in sequence: adopting 17Alpha-hydroxyl progesterone as a raw material and utilizing alkali as a solvent; eliminating under the effect of lewis acid; carrying out a reduction reaction; neutralizing by acid; washing by alkali liquor; decolouring by ethanol; and recrystallizing to obtain the progesterone. Compared with the prior art, the novel process provided by the invention has the advantages that the raw material is easy to obtain, the process flow is simple and short, the operation is simple, the industrial production can be carried out, the yield is up to more than 71%, the melting point is 128 to 130 DEG C, the HPLC (High Performance Liquid Chromatography) is more than 99%, the product is in off-white colour, the product is high in quality, and the preparation cost is low.

Description

Technical field: [0001] The invention relates to a new process for preparing progesterone, which belongs to the technical field of organic synthesis. technical background: [0002] Progesterone is also called progesterone, progesterone, progesterone, and gestational hormone. It is a progestin. Its chemical name is preg-4-ene-3,20-dione. Its English name is Progesterone. [0003] [0004] Progesterone is a steroid hormone with 21 carbon atoms secreted by ovarian luteal cells. It is also an intermediate product in the synthesis of all steroid hormones and is one of the progestogens. There are two crystal forms, α-type and β-type. The two crystal forms have the same physiological activity. The α-type is precipitated from dilute ethanol and is an orthorhombic white prismatic crystal. It is white needle-like crystal of inter-crystal system, both of which are insoluble in water, but soluble in ethanol, ether, chloroform, acetone, dioxane and concentrated sulfuric acid. [000...

Claims

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Application Information

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IPC IPC(8): C07J7/00
Inventor 刘志强杨昌勇
Owner HUNAN KEYUAN BIO PRODS