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A kind of preparation method of progesterone

A progesterone and compound technology, applied in the field of preparation of organic steroids, can solve the problems of lack of competitiveness, environmental pollution, long production cycle, etc., and achieve the effect of simple process, environment-friendly and easy operation

Active Publication Date: 2017-08-15
ZHEJIANG ZHUJI UNITED CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Yet the method for extracting diosgenin (VIII) from yam plant has following defect: (1) yam resource is limited; (2) production cycle is long; (3) yield is low; (4) use a large amount of organic solvents to exist production safety Hidden dangers and serious environmental pollution
[0013] The physical and chemical properties of these diene ether compounds (XIV~XVIII) seriously limit their application in industrialized production
In addition, the method uses expensive methyl iodide as a methylation reagent, making the method uncompetitive in terms of auxiliary material costs

Method used

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  • A kind of preparation method of progesterone
  • A kind of preparation method of progesterone
  • A kind of preparation method of progesterone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: (E)-17-formamido-tosylmethylene-3-(2,2-dimethyl-1,3-dioxopropyl)androst-5-ene (Compound IV ) Preparation 1

[0030] Under a dry ice-acetone bath, THF (40mL), TosMIC (1.95g), compound (II) (3.73g), and potassium tert-butoxide (2.48g) were sequentially added to react for 2h. Extracted with methyl chloride, and the organic layer was dried and concentrated to obtain 5.4 g of compound (IV) as a pale yellow foamy solid.

Embodiment 2

[0031] Example 2: (E)-17-formamido-tosylmethylene-3-(2,2-dimethyl-1,3-dioxopropyl)androst-5-ene (Compound IV ) Preparation 2

[0032] Under the dry ice-acetone bath, add toluene (50mL), TosMIC (2.93g), compound (II) (3.73g), lithium tert-butoxide (1.77g) in sequence, react for 2h, pour the reaction solution into water, and use two Extracted with methyl chloride, and the organic layer was dried and concentrated to obtain 5.3 g of compound (IV) as a pale yellow foamy solid.

Embodiment 3

[0033] Example 3: (E)-17-isocyano-p-toluenesulfonylmethylene-3-(2,2-dimethyl-1,3-dioxopropyl)androst-5-ene (Compound V ) Preparation 1

[0034] Compound (IV) (6.38g) prepared above was dissolved in tetrahydrofuran (50mL), diisopropylamine (4.9mL) was added dropwise at -10°C, phosphorus oxychloride (1.1mL) was added dropwise, and reacted for 2h. The reaction solution was poured into 100 mL of ice water containing 5 g of sodium bicarbonate, filtered, washed with water, and dried to obtain 5.9 g of yellow solid compound (V).

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Abstract

The invention discloses a preparation method for progesterone. The method comprises the following steps: with the compound 3-(2,2-dimethyl-1,3-dioxopropyl)-5-en-17-one (II) as a starting raw material, subjecting the starting raw material and a sulfonylmethyl isocyanide compound (III) to a condensation reaction under the action of alkali so as to prepare a formamido-sulfonylmethylene compound (IV); subjecting the compound (IV) to dehydration so as to obtain an isocyano-sulfonylmethylene compound (V); carrying out a reduction reaction on the compound (V) so as to prepare an isocyano-sulfonylmethyl compound (VI); subjecting the compound (VI) to methylation so as to obtain an isocyano-sulfonylethyl compound (VII); and carrying out hydrolysis on the compound (VII) so as to obtain the target products progesterone (I). The preparation method is simple in integral process, easy to operate, low in cost and suitable for large-scale production.

Description

technical field [0001] The invention relates to a preparation method of organic steroids, in particular to a preparation method of progesterone. Background technique [0002] Progesterone (Progesterone), chemical name pregn-4-ene-3,20-dione, structural formula is as follows: [0003] [0004] Progesterone was discovered in 1933 and successfully isolated from pregnant urine in 1934. 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. Progesterone is clinically used in the reactive diagnosis of threatened abortion, habitual abortion and other amenorrhea or the cause of amenorrhea. [0005] In addition, progesterone is the precursor of corticosteroids, androgens and estrogens, and plays an important role in the field of drug synthesis. [0006] Extracting progesterone from animals has the disadvantages of small amount...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J7/00C07J41/00
CPCC07J7/002C07J41/0033C07J41/0094
Inventor 梁小敏周君津腾海鸽周萍陈邦池
Owner ZHEJIANG ZHUJI UNITED CHEM
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