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Process for production of steroids

A compound, cholestanoic acid technology, applied in the field of preparation of steroids, can solve problems such as limited application

Inactive Publication Date: 2009-02-25
MITSUBISHI CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Also, synthesis of cholesta-4,6,24-trien-3-one as an intermediate when using cholesta-5,7,24-trien-3β-ol as a raw material as various steroid medicines Intermediates are useful, but have historically been obtained from raw materials of natural origin and prepared through lengthy reaction steps, thus limiting their use in terms of cost and quantity

Method used

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preparation example Construction

[0307] The cholesta-5,7,24-trien-3β-ol used as a raw material in the production method of the present invention itself is a known substance. For example, it can be produced by metabolically engineering a fungus that produces ergosterol via zymosterol to create a mutant strain, culturing the mutant strain to obtain a culture, and collecting it from the culture. For details of the production method, for example, methods described in JP-A-5-192184 and JP-A-2004-141125 can be referred to.

[0308] Preparation of cholesta-4,7,24-triene-3 represented by the following formula (3) from cholesta-5,7,24-trien-3β-ol represented by the following formula (2) - Keto steps

[0309]

[0310] As can be seen from the above reaction formula, step 1 of the present invention is to simultaneously carry out the oxidation of the 3-position hydroxyl and the 5-position double bond of cholesta-5,7,24-triene-3β-alcohol (hereinafter sometimes referred to as "compound 2") A step toward the isomerizat...

Embodiment 1

[0518]

[0519] 4.38g (11.47mmol) of cholesta-5,7,24-triene-3β-alcohol (compound 2) and 11.24g (114.66mmol) of cyclohexanone were dissolved in 44ml of toluene, and the reduction was repeated several times at room temperature. After pressure degassing and nitrogen substitution, 1.17 g (5.74 mmol) of aluminum isopropoxide was added at room temperature, and the mixture was stirred at 112° C. for 2 hours under a nitrogen atmosphere. After the reaction, the reaction liquid was cooled to room temperature, 2.3ml of water was added and stirred at room temperature for 1 hour. The precipitated precipitate was filtered, the filtrate was concentrated, and it was separated and purified by silica gel column chromatography to obtain 4.01 g of cholesta-4,7,24-trien-3-one (compound 3). The yield of isolated and purified compound 2 was 92%, and its NMR shift value (δppm) is shown below.

[0520] δ: 0.60(s, 3H, 18-H), 0.96(d, 6.5Hz, 3H, 21-H), 1.18(s, 3H, 19-H), 1.61(s, 3H, 26-H), 1.69 (s, 3...

Embodiment 2

[0522]

[0523] 3.49g (9.18mmol) of cholesta-4,7,24-triene-3-one (compound 3) obtained by the method of Example 1 was dissolved in 70ml of methanol, and several times of vacuum decompression were carried out at room temperature. After gas and nitrogen substitution, 2.53 g (38.40 mmol) of 85% granular potassium hydroxide was added, and the mixture was stirred at 64° C. for 7 hours under a nitrogen atmosphere. After the reaction, the reaction liquid was cooled to room temperature, 2.37 g of acetic acid was added and stirred at room temperature for 0.5 hours. Next, methanol was distilled off under reduced pressure, water was added, and extracted with ethyl acetate, the organic phase was washed with water, dried, concentrated, and separated and purified by silica gel column chromatography to obtain 3.13 g of cholestan-4,7,24- Trien-3-ones (Compound 4). The yield of isolated and purified compound 3 was 90%, and its NMR shift value (δppm) is shown below.

[0524] δ: 0.76(s, 3H, ...

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Abstract

The invention provides a novel process for the production of steroids, namely, a process for the production of 5ss-3,7 -dioxocholanoic acid or ester derivatives thereof which comprises using as the raw material a sterol having double bonds at the 5- and 24-positions selected from among cholesta -5,7,24-trien-3ss-ol, ergosta-5,7,24(28)-trien-3ss-ol, desmo- sterol, fucosterol, and ergosta-5,24(28)-dien-3ss-ol and conducting the following four steps: (I) the step of conducting the oxidation of 3-position hydroxyl and the isomerization of double bond from the 5-position to the 4-position (II) the step of converting the group at the 24-position into carboxyl or a carboxylic ester group by oxidative cleavage of the side chain, (III) the step of introducing an oxygen-containing functional group to the 7-position, and (IV) the step of constructing 5ss-configuration by reductive saturation of the 4-position double bond.

Description

technical field [0001] The present invention relates to a method for preparing steroids, in particular, to a method for preparing 3,7-dioxo-5β-cholestanoic acid or its ester derivatives, which is obtained by adding a steroid with a double bond at the 4-position The compound is reductively saturated to carry out the construction of the 5β stereo. More specifically, it relates to a method for preparing 3,7-dioxo-5β-cholestanoic acid or its ester derivatives. The method is based on the 5-position and 24 Cholesta-5,7,24-trien-3β-ol, or ergosta-5,7,24(28)-trien-3β-ol, streptosterol or fucosterol of sterols with a double bond , Ergosta-5,24(28)-diene-3β-alcohol is raw material, and through following 4 steps, namely: [0002] (1) carry out the step of the oxidation of 3-position hydroxyl and the isomerization of 5-position double bond to 4-position; [0003] (II) a step of changing the 24-position into a carboxyl group or an ester derivative thereof by oxidative cleavage of the sid...

Claims

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Application Information

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IPC IPC(8): C07J9/00C07J1/00C07J17/00C07J41/00B01J21/08B01J23/44
Inventor 竹原润藤原尚哉远藤恭子河井润也细川明美住谷直子
Owner MITSUBISHI CHEM CORP
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