Preparation method of dydrogesterone intermediate

Abstract

The invention discloses a preparation method of a dydrogesterone intermediate. The preparation method is characterized by comprising the following steps: dissolving 5,7-diene steroid compound in an organic solvent to obtain a solution as a raw material; and carrying out a photocatalytic reaction and separating to obtain the dydrogesterone intermediate, wherein the 5,7-diene steroid compound is 7-dehydropregnenolone acetate, pregna-5,7-diene-3,20-diketodivinyl ketal, 7-dehydropregnenolone, ergosterol or pregna-5,7-diene-3,20-diketo-3-vinyl ketal, and a lamp used in the photocatalytic reaction comprises an LED ultraviolet lamp with the wavelength range of 295-335 nm. The preparation method of the dydrogesterone intermediate is high in yield, low in cost, safer in preparation and friendlier to environment.

Description

technical field [0001] The present invention relates to the technical field of dydrogesterone intermediates, in particular to a preparation method of a dydrogesterone intermediate. Background technique [0002] Dydrogesterone (Dydrogesterone), also known as dehydroprogesterone, CAS 152-62-5, chemical name is 9β,10α-pregnant-4,6-diene-3,20-dione. Dydrogesterone is a highly potent progesterone that is clinically used to treat amenorrhea, endometriosis, prevent functional bleeding and threatened abortion. [0003] Pregnantyl Photosterol Acetate (CAS 1788-02-5), 9β,10α-Pregnant-5,7-diene-3,20-dione diethylketal (CAS 5488-51-7), Pregnant Photosterol (CAS 1819-14-3), Photosterol L 2 (CAS 494-69-1), 9β,10α-pregna-5,7-diene-3,20-dione-3-ethylene ketal (CAS 32164-72-0) are synthetic dydrogesterone, respectively key intermediates of different synthetic routes. [0004] In the traditional synthetic method of dydrogesterone products, as reported by the Royal Netherlands Society of C...

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Problems solved by technology

[0004] In the traditional synthetic method of dydrogesterone product, as reported by Royal Netherlands Chemical Society (1960,79, P771), Solvay Pharmaceutical Company of Holland produces the bulk drug of dehydroprogesterone product, and the processing route that adopts is: The by-product of vitamin D production - photosterol is used to produce dehydroprogesterone products through chemical reactions such as Woshi oxidation, rearrangement, lithium ammonia reduction, ozonation, 20-position complexation, oxidation, and dehydrogenation, with a total yield of about 3 %, its defect is that the reaction steps are longer, the yield is lower, and the cost is higher, and it uses poisonous and harmful materials such as sodium dichromate, pure benzene, chloroform, and flammable and explosive materials such as ether and petroleum ether, and some raw materials are not easy to obtain , part of the reaction conditions are harsh (ozone is used to modify the side chain at the 17th position, and the reaction temperature requires -80°C)

[0005] The traditional synthesis method of dydrogesterone is very difficult to realize. At present, the key intermediates of domestic industrial synthesis of dydrogesterone cannot be mass-produced due to low yield and high energy consumption, and high-pressure mercury lamps are used in industrial production. There are certain security risks

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