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A method for preparing progesterone using 1,4-androstenedione as raw material

A technology of androstenedione and progesterone, which is applied in the field of preparation of progesterone, can solve the problems of large environmental pollution and restrictions, and achieve the effects of low price, low manufacturing cost and high yield

Active Publication Date: 2015-12-02
HUNAN KEYUAN BIO PRODS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017]In addition, the process of diosgenin, sisal saponin and caraf saponin involves chemical reagents such as chromic anhydride, which causes serious environmental pollution. , must be increasingly restricted

Method used

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  • A method for preparing progesterone using 1,4-androstenedione as raw material
  • A method for preparing progesterone using 1,4-androstenedione as raw material
  • A method for preparing progesterone using 1,4-androstenedione as raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 1) Add 10g of 1,4-androstenedione (4-AD), 10mL of absolute ethanol, 10mL of triethyl orthoformate, and 0.1g of p-toluenesulfonic acid into a dry three-necked flask, and stir , pass nitrogen protection, heat up to 40 o C, and keep warm for 3 hours; Then, neutralize the reaction solution with absolute ethanol containing pyridine, adjust the pH to 7.0, and cool to 0 o C, suction filtration; then wash the crystals with absolute ethanol containing pyridine, and dry to constant weight to obtain the enol ether of 4-AD, namely 3-ethoxy-androst 3,5-dien-20-one 10.5 g;

[0040] 2) Put 18.0g of (1-methoxyethyl)-triphenylphosphine tetrafluoroborate into another dry three-necked flask, then add 100mL of anhydrous tetrahydrofuran into it, and pass through nitrogen protection, Cool down to -50 o C, add 4.0g of potassium tert-butoxide in batches to the system, and stir at this temperature for 2 hours; then, add enol ether 3-ethoxy-androster 3,5 with 10.5g of 4-AD dissolved in the sy...

Embodiment 2

[0042] 1) Add 10g of 4-AD, 10mL of anhydrous methanol, 10mL of trimethyl orthoformate, and 0.05g of concentrated sulfuric acid into a dry three-necked flask in turn, stir, pass through nitrogen protection, and stir at 25°C for 3 hours; Then, neutralize with absolute ethanol containing pyridine, adjust the pH to 7.0, cool to -10 o C, suction filtration; then wash the crystals with absolute ethanol containing pyridine, and dry to constant weight to obtain 10.1 g of enol ether 3-ethoxy-androst 3,5-dien-20-one of 4-AD;

[0043] 2) Put 18.0g of (1-methoxyethyl)-triphenylphosphine tetrafluoroborate into another dry three-necked flask, then add 100mL of anhydrous tetrahydrofuran into it, pass through nitrogen protection, and cool down to -80 o C, dropwise add n-butyl lithium solution containing 44mmol to the system, stir at this temperature for 1 hour; then slowly raise the temperature of the system to -40 o C, and 20mL anhydrous tetrahydrofuran solution of enol ether 3-ethoxy-andr...

Embodiment 3

[0045]1) Add 20g of 1,4-androstenedione (4-AD), 20mL of anhydrous tetrahydrofuran, 20mL of triethyl orthoformate, and 0.2g of p-toluenesulfonic acid into a dry three-necked flask, and stir , pass nitrogen protection, heat up to 50 o C, and keep warm for 3 hours; Then, neutralize the reaction solution with absolute ethanol containing pyridine, adjust the pH to 7.0, and cool to 0 o C, suction filtration; then wash the crystals with absolute ethanol containing pyridine, and dry to constant weight to obtain the enol ether of 4-AD, that is, 3-ethoxy-androst 3,5-dien-20-one 21.8 g;

[0046] 2) Put 36.0g of (1-methoxyethyl)-triphenylphosphine tetrafluoroborate into another dry three-necked flask, then add 200mL of anhydrous tetrahydrofuran into it, pass through nitrogen protection, and cool down to -50 o C. Add 88 mmol of sodium methoxide solution to the system in batches, and stir at this temperature for 2 hours; then, add enol ether 3-ethoxy-androster 3,5- 40mL of anhydrous tet...

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Abstract

The invention discloses a method for preparing progesterone by taking 1,4-androstenedione as a raw material, which comprises the following steps: 1) dissolving 1,4-androstenedione into an organic solvent, adding the acid of trimethyl orthoformate or triethyl orthoformate, and introducing nitrogen to protect the 1,4-androstenedione to synthesize the enol ether of 1,4-androstenedione, namely 3-methoxy-androstane 3,5-diene-20-ketone; and 2) dispersing (1-methoxy ethyl)-triphenylphosphine salt in a reaction medium, an organic solvent, adding alkali at low temperature, performing a Wittig reaction of the 3-methoxy-androstane 3,5-diene-20-ketone synthesized in the step 1), and purifying and crystallizing to obtain progesterone. By adopting the 1,4-androstenedione as the raw material, the method solves the problem that of lack in raw materials for synthesizing steroid drugs such as progesterone, and improves the utilization rate of 1,4-androstenedione and the yield of progesterone; the preparation process is simple.

Description

technical field [0001] The invention relates to a method for preparing progesterone, in particular to a method for preparing progesterone by using 1,4-androstenedione as a raw material. Background technique [0002] Progesterone is a natural progestin secreted by the corpus luteum of the ovary. It has a significant morphological effect on the estrogen-stimulated endometrium in vivo and is necessary to maintain pregnancy. [0003] Progesterone is clinically used in the reactive diagnosis of threatened abortion, habitual abortion and other amenorrhea or the cause of amenorrhea. [0004] At present, the synthetic method of progesterone has four following synthetic methods, specifically: [0005] (1) Synthesis of progesterone with diosgenin as raw material, the reaction equation is as follows: [0006] [0007] (2) Synthesis of progesterone with ergosterol as raw material, the reaction equation is as follows: [0008] [0009] (3) Synthesis of progesterone with stigmast...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J7/00
Inventor 林文彬刘志强
Owner HUNAN KEYUAN BIO PRODS
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