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Preparation method of progestational hormone intermediate

A progestogen and intermediate technology, applied in the field of medicinal chemistry, can solve the problems of poor hydrogenation selectivity, cumbersome operation, low yield and the like, and achieve the effects of improving yield and quality, simple preparation process and reducing cost

Inactive Publication Date: 2013-05-08
YANGZHOU PHARM CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of this method is that the selectivity of hydrogenation is relatively poor, and the purity of the product generally can only reach 80-90%. Big risk. In actual production, the upper reaction liquid can only be simply layered and extracted. The recovery of the catalyst needs to be complicated and cumbersome before it can be applied. The quality and catalytic activity of the catalyst are difficult to control, and the recovery cost is high.
[0003] It is also reported that the formula Active groups (such as carbonyl) are protected and hydrogenated under the catalysis of Pd-calcium carbonate, but after hydrogenation, hydrolysis is required to remove the protective group, which has the disadvantages of cumbersome operation and low yield

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  • Preparation method of progestational hormone intermediate
  • Preparation method of progestational hormone intermediate
  • Preparation method of progestational hormone intermediate

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preparation example Construction

[0040] Through the preparation method of the progesterone intermediate provided by the invention, the formula The progesterone intermediate can be directly used in the production of subsequent steps without purification, thereby improving the yield and quality of the final product and effectively reducing costs.

[0041] Specifically, the formula The compound of the compound is passed through a composite catalyst containing palladium in a low-carbon alcohol solvent to carry out a hydrogenation reaction; the reaction solution is filtered and then concentrated under reduced pressure to obtain the formula progesterone intermediates.

[0042] Wherein, the composite catalyst containing palladium is preferably a palladium-carbon catalyst. Considering the use effect of the catalyst and the reaction speed of the substrate, the content of the catalyst is preferably 1% to 10% by weight of palladium, and the catalyst consumption is preferably that of the substrate after drying. 1 to...

Embodiment 1

[0048] Put methanol 150ml into the reaction bottle, the compound formula 2 (R1=OCOCH 3 ,R2=C 2 h 5 ,R3=OCH 3 ) 24g, and the palladium-carbon catalyst (5% weight of palladium in the palladium-carbon catalyst) which is 5% weight of the substrate after dehydration, start timed reaction at 40 ℃ for 2 hours, and calculate to reach the theoretical hydrogen absorption amount, take the heat Press filtration to recover the catalyst. The filtrate was concentrated under reduced pressure until solids were precipitated, refrigerated to crystallize, filtered, and the solids were dried to obtain 20.6 g of the hydrogenated product as white crystals, HPLC purity: 99.2%. HPLC spectrum see figure 1 .

Embodiment 2

[0050] Put methanol 150ml into the reaction bottle, the compound formula 2 (R1=OCOCH 3 ,R2=C 2 h 5 ,R3=OCH 3) 24g, and the palladium-carbon catalyst (5% weight of palladium in the palladium-carbon catalyst) that is 10% by weight of the substrate after dehydration. At 50°C, start the timing reaction for 1 hour, and calculate the theoretical hydrogen absorption, multiply by Filtration under hot pressure to recover the catalyst. The filtrate was concentrated under reduced pressure until solids were precipitated, refrigerated to crystallize, filtered, and the solids were dried to obtain 19.2 g of the hydrogenated product in the form of white crystals with an HPLC purity of 99.3%. HPLC spectrum see figure 2 .

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Abstract

The invention relates to a preparation method of a progestational hormone intermediate as shown in formula I. The preparation method comprises the following steps of adding a compound shown in formula II and palladium-containing composite catalyst into a low-carbon alcohol solvent, performing hydrogenation reaction for 0.5 to 5 hours at a temperature between room temperature and 150 DEG C; filtering the reaction liquid, and decompressing and concentrating to obtain the progestational hormone intermediate in formula I, wherein R1 is OH, OCOCH3, O and OCH3, R2 is H, CH3 and C2H5, and R3 is H, CH3, OCH3, and OC2H5. Compared with the prior art, by adopting the preparation method of the progestational hormone intermediate disclosed by the invention, the purity of a product is over 98 percent, and the product can be directly used in the production of the subsequent step without purification, so that the yield and the quality of a final product can be improved, and the cost can be effectively reduced.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of a progesterone intermediate. Background technique [0002] Mode is an important steroidal progesterone hormone intermediate for the following formula The levonorgestrel shown, the following formula The desogestrel shown, the following formula The synthesis of multiple important drugs such as gestodene shown, the traditional preparation method is the following formula The compounds shown are starting materials, catalyzed by hydrogenation with Raney Ni. The disadvantage of this method is that the selectivity of hydrogenation is relatively poor, and the purity of the product generally can only reach 80-90%. Big risk, in actual production, the upper layer reaction solution can only be simply layered and extracted, and the recovery of the catalyst needs to go through more complex and tedious treatment before it can be applied mechan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
Inventor 扈田进
Owner YANGZHOU PHARM CO LTD