Preparation method for trenbolone acetic ester

A technology of dragon acetate and temporolone, which is applied in the field of preparation of steroid compound tambolone acetate, can solve problems such as inability to obtain solids, and achieves the effects of short reaction route, high yield and broad application prospects

Active Publication Date: 2012-04-04
湖南科益新生物医药有限公司
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Problems solved by technology

But there is certain defect in this synthetic method, wherein there are two-step reaction process such as potassium borohydride reduction (step 2.) and hydrolysis (step 3.) can not obtain solid, is unfavorable for carrying out quality control to intermediate; Dichlorodicyanobenzoquinone (DDQ ) dehydrogenation process (step ④) using very toxic benzene as a solvent has certain limitations for the realization of industrial production

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  • Preparation method for trenbolone acetic ester
  • Preparation method for trenbolone acetic ester
  • Preparation method for trenbolone acetic ester

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preparation example Construction

[0044] In order to solve the shortcomings of the existing method for preparing tambolone acetate, such as long synthetic route, complicated operation and low yield, the present invention provides a short reaction route, high reaction selectivity, less by-products and high yield. Preparation method of tambolone acetate. The method is based on 17β-hydroxyl-estro-4,9-dien-3-one as a starting material (compound 2), and comprises the following steps in turn:

[0045]

[0046] 1) Esterification of the 17β hydroxyl group of compound 2 and the esterification of the 3-position enol to obtain 5(10), 9(11)-estratriene-3, 17β-diol diacetate (compound 3);

[0047] 2) The 3-position enol ester of compound 3 was hydrolyzed to obtain 17β-hydroxy-estro-5(10), 9(11)-dien-3-one acetate (compound 4);

[0048] 3) The 5(10), 9(11) conjugated double bonds of compound 4 were dehydrogenated by dichlorodicyanoquinone (DDQ) to obtain tambolone acetate (compound 1).

[0049] The following examples a...

Embodiment 1

[0051] Embodiment 1, prepare tamburone acetate

[0052] Prepare tambolone acetate with the method of the present invention, and concrete method comprises the following steps:

[0053] 1) Obtaining of 3,5(10),9(11)-estratriene-3,17β-diol diacetate (compound 3)

[0054] Starting with 17β-hydroxy-estr-4,9-dien-3-one (compound 2, the starting material is 3-methoxy-estr-2,5(10)-diene- 17β-alcohol is used as a raw material, which can be prepared according to existing methods, such as the method reported in the literature (Wang Ruibin et al., Chinese Journal of Medicinal Chemistry, 1994, 4(3): 187-189), with a yield of 68.5% and a melting point of: 184-187℃, specific rotation: (C=1%, CHCl 3 ), content: 98.6% (HPLC); this raw material can also be obtained commercially, such as Beijing Ganxing Chemical Factory, etc.

[0055] Esterify its 17β-hydroxyl and simultaneously esterify the 3-position enol to obtain 3,5(10),9(11)-estratriene-3,17β-diol acetate (compound 3) The chemical rea...

Embodiment 2

[0074] Embodiment 2, preparation tempbolone acetate

[0075] Prepare tambolone acetate with the method of the present invention, and concrete method comprises the following steps:

[0076] 1) Obtaining of 3,5(10),9(11)-estratriene-3,17β-diol diacetate (compound 3)

[0077]Starting from 17β-hydroxy-estr-4,9-dien-3-one, esterify its 17-hydroxyl group and simultaneously esterify its 3-position enol to obtain 3,5(10),9(11)- Estratriene-3, the chemical reaction formula of 17β-diol diacetate (compound 3) is identical with embodiment 1, and concrete synthetic method is as follows:

[0078] A) Put acetic anhydride (600mL, 6.35mol), acetyl chloride (400mL, 5.61mol) and pyridine (10mL) into the reaction vessel in turn, put compound 2 (50g, 183.57mmol) under stirring, heat up to 80°C, and protect it under nitrogen keep the reaction for 1 hour;

[0079] B) When the heat preservation is over, cool the reaction solution to 20°C, slowly pour the reaction solution into 1200mL ice water whi...

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Abstract

The invention provides a preparation method for trenbolone acetic ester. In the preparation method, 17beta-hydroxy-estra-4,9-diene-3-keton as an initiative material (compound 2). The method sequentially comprises the following steps of: 1) esterifying 17-position hydroxyl and 3-position enol of the compound 2 to obtain 3,5(10),9(11)-estratriene-3,17beta-glycol diacetic ester (compound 3); 2) hydrolyzing 3-position enol ester of the compound 3 to obtain 17beta-hydroxy-estra-5(10),9(11)-diene-3-ketone acetic ester (compound 4); and 3) dehydrogenizing 5(10),9(11) conjugated double bond of the compound 4 by using dichloro dicyan quinone (DDQ) to obtain the trenbolone acetic ester (compound 1). The method plays an important role in preparation of medicines (such as finaplix, Revalor, Parabol 25 mg, Forplix, Toreter and the like) by using trenbolone acetic ester as the raw material medicine and has wide application prospect.

Description

technical field [0001] The invention relates to a preparation method of a steroid compound in the field of chemical synthesis, in particular to a preparation method of a steroid compound tambolone acetate as a bulk drug. Background technique [0002] Trenbolone Acetate (Trenbolone Acetate, TBA), chemical name is 17β-acetoxy-estro-4,9,11-trien-3-one, and its structural formula is as shown in formula I: [0003] [0004] Tambolone acetate is a kind of anabolic hormone with good effect, which was successfully developed by Roussel UCLAF company in France in the 1970s. Tambolone acetate can significantly promote the growth of beef cattle, and can also significantly reduce the ratio of meat to feed and improve meat quality. As a growth agent for beef cattle, it has been produced and widely used abroad, especially in North America. [0005] In 2002, Zhang Huyue et al. (Journal of Fudan University (Medical Edition) 2002, 29 (3): 211-212) reported a preparation method of tambolon...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
Inventor 高建永刘文秀
Owner 湖南科益新生物医药有限公司
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