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A kind of synthetic method of 6-ketoestradiol

A technology for the synthesis of ketone estradiol, which is applied in the direction of chemical instruments and methods, steroids, estrone derivatives, etc., can solve the problems of increased production difficulty, high production risk, long steps, etc., and achieve cost Low cost, green reaction conditions and mild process conditions

Active Publication Date: 2022-06-24
HUNAN NORCHEM PHARMACEUTICAL CO LTD
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0008] The above scheme needs to use active reagents such as butyllithium, which is costly and dangerous in production, and the steps are longer, making production more difficult

Method used

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  • A kind of synthetic method of 6-ketoestradiol
  • A kind of synthetic method of 6-ketoestradiol
  • A kind of synthetic method of 6-ketoestradiol

Examples

Experimental program
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Embodiment 1

[0022] 1. Reduction reaction

[0023] In the reaction flask, add 50 g of compound 1, add 100 mL of THF and 100 mL of methanol to dissolve, cool down to 0-10 °C, add 5 g of sodium borohydride, keep stirring for 2 h, TLC shows that the reaction is complete, add 10 mL of glacial acetic acid dropwise to quench the reaction, add 100 mL of water, the system was concentrated under reduced pressure at 50 °C until solvent-free, the solid was precipitated, cooled to room temperature, stirred for 1 h, filtered, and the filter cake was washed with water and dried to obtain compound 2 with a yield of 96% and a purity of 98%.

[0024] 2. Oxidation reaction

[0025] In the reaction flask, add 30 g of compound 2, 100 mL of propylene acetate, and 3 g of p-toluenesulfonyl chloride p-TS. Under nitrogen protection, heat to 60 °C for 6 h. After the reaction is completed, the propylene acetate is concentrated under reduced pressure, and 200 mL of acetic acid is added. Ethyl ester, lowered and warm...

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Abstract

The invention belongs to the technical field of preparation of steroid hormone intermediates, and in particular relates to a synthesis method of 6-ketoestradiol, which uses compound 1 as a raw material, and obtains 6-ketoestradiol through the following reaction route, The reaction route is as follows: the raw material of the present invention is different from estrone, has low price, wide sources and low cost. In the present invention, by optimizing the reaction route, when the 6-position carbonyl is introduced, the 6-position is the only active site, greatly increasing the selectivity of oxidation, and the reaction conditions are also green and environment-friendly. The invention provides a brand-new synthesis route of 6-ketoestradiol, which has mild process conditions, is environmentally friendly, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation of a steroid hormone intermediate, in particular to a method for synthesizing 6-ketoestradiol. Background technique [0002] Antiestrogen therapy is an important method of endocrine therapy for breast cancer, and pure antiestrogens are a class of drugs that have high affinity with estrogen receptors without any agonistic activity, and have significant curative effects in clinical pharmacological tests. . Therefore, the synthesis of pure antiestrogens has also attracted much attention, and 6-ketoestradiol is an important intermediate in the synthesis of 7a-substituted estradiol pure antiestrogen molecules, such as the anticancer drug fulvestrant. [0003] Synthesis of estrogen drug intermediate 6-ketoestradiol, Liang Zhanchao et al., Synthetic Chemistry, Vol. 19 in 2011, discloses a traditional method for synthesizing 6-ketoestradiol, starting from estrone, through reduction, Steps such as es...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J1/00
CPCC07J1/007
Inventor 唐杰刘喜荣曾春玲李凯
Owner HUNAN NORCHEM PHARMACEUTICAL CO LTD
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