Preparation method of 25-hydroxy-7-dehydrocholesterol

A technology for dehydrocholesterol and hydroxyl group, which is applied in the field of preparation of 25-hydroxy-7-dehydrocholesterol, can solve the problems of low product purity, complicated preparation process and high preparation cost, and achieves a simple process, environmental protection process and low cost. Effect

Pending Publication Date: 2022-07-05
上海其正医药科技有限责任公司
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  • Description
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Problems solved by technology

[0015] In view of this, the present invention provides a method for preparing 25-hydroxy-7-dehydrocholesterol, which solves the problems of complicated preparation process, low product purity and high preparation cost

Method used

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  • Preparation method of 25-hydroxy-7-dehydrocholesterol
  • Preparation method of 25-hydroxy-7-dehydrocholesterol
  • Preparation method of 25-hydroxy-7-dehydrocholesterol

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preparation example Construction

[0053] A preparation method of 25-hydroxy-7-dehydrocholesterol, the preparation method comprises the following steps:

[0054] 1) 21-hydroxy-20-methylpregna-4-en-3-one is reacted with tetrachlorobenzoquinone to obtain 21-acetoxy-20-methylpregna-4,6-diene-3 -ketone;

[0055] 2) hydrolyzing 21-acetoxy-20-methylpregna-4,6-dien-3-one to obtain 21-hydroxy-20-methylpregna-4-en-3-one;

[0056] 3) 21-hydroxy-20-methylpregna-4-en-3-one is reacted to obtain

[0057] 4) will reacted with methyl ketene to obtain

[0058] 5) will Methyl Grignard reagent and tetrahydrofuran react to give 25-hydroxy-7-dehydrocholesterol.

[0059] As a preferred version of the present invention, the reaction in the step 3) includes a sulfonation reaction, a double bond transposition reaction, a reduction reaction, an acetylation reaction and an iodination reaction that are carried out in sequence;

[0060] The sulfonation reaction is carried out by 21-hydroxy-20-methylpregna-4-en-3-one and a sulfo...

Embodiment 1

[0082] 1. Synthesis of 21-acetoxy-20-methylpregna-4,6-dien-3-one

[0083] In a 2000mL three-necked flask, put 200g of 21-hydroxy-20-methylpregna-4-en-3-one, 600mL of acetic acid, 200mL of toluene, 164g of tetrachlorobenzoquinone, and react at 110°C for 6h. Cooled to room temperature, suction filtered, the filtrate was rotary evaporated to dryness, dissolved in 600 mL of acetone, added with 2000 mL of a 3.5% aqueous sodium hydroxide solution to separate out, suction filtered, and dried to obtain 199 g of product. The molar yield was 88.7%. HNMR (500MHz, CDCl 3 )δ:6.11(m, 2 H),5.66(m, 1 H),4.05(m, 1 H),3.77(m, 1 H), 2.06(s, 3 H)1.00(d, 3 H),0.98(d, 3 H),0.72(s, 3 H).

[0084] 2. Hydrolysis reaction

[0085] 199 g of 21-acetoxy-20-methylpregna-4,6-dien-3-one was dissolved in 700 mL of methanol, 200 mL of 9.7% sodium hydroxide solution was added dropwise, and the reaction was carried out at 0° C. for 2 h. After the reaction, methanol was evaporated, extracted with dich...

Embodiment 2

[0101] 1. Synthesis of 21-acetoxy-20-methylpregna-4,6-dien-3-one

[0102]In a 2000ml three-necked flask, put 200g of 21-hydroxy-20-methylpregna-4-en-3-one, 600ml of acetic acid, 200ml of toluene, 164g of tetrachlorobenzoquinone, and react at 110°C for 6h. The reaction was completed, cooled down, suction filtered, the filtrate was rotary evaporated to dryness, dissolved in 600 ml of acetone, added with 2000 ml of a 3.5% aqueous sodium hydroxide solution to separate out, suction filtered, and dried to obtain 199 g of product. The molar yield was 88.7%. HNMR (500MHz, CDCl 3 )δ:6.11(m, 2 H),5.66(m, 1 H),4.05(m, 1 H),3.77(m, 1 H), 2.06(s, 3 H)1.00(d, 3 H),0.98(d, 3 H),0.72(s, 3 H). Its spectrum is attached figure 2 shown.

[0103] 2. Hydrolysis reaction

[0104] 199 g of 21-acetoxy-20-methylpregna-4,6-dien-3-one was dissolved in 700 ml of methanol, 200 ml of sodium hydroxide solution with a mass fraction of 9.7% was added dropwise, and the reaction was stirred. After...

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Abstract

The invention belongs to the technical field of cholesterol synthesis, and particularly discloses a preparation method of 25-hydroxy-7-dehydrocholesterol. The preparation method of the 25-hydroxy-7-dehydrocholesterol, provided by the invention, comprises the following steps: 1) carrying out reaction, hydrolysis, sulfonation and double-bond transposition on 4-BA and chloranil, and carrying out 3-position carbonyl reduction reaction, acetylation, iodine substitution, methyl ketene addition reaction and methyl Grignard reagent addition reaction by utilizing carbonyl reductase or sodium borohydride to obtain the 25-hydroxy-7-dehydrocholesterol; or 2) 4-BA and chloranil are subjected to a reaction, hydrolysis, iodine substitution, double bond transposition, a reduction reaction, acetylation, a methyl ketene addition reaction and a methyl Grignard reagent addition reaction, and 25-hydroxy-7-dehydrocholesterol is obtained. The synthesis method is simple in process, high in product purity, low in cost, environment-friendly in process and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of cholesterol synthesis, in particular to a preparation method of 25-hydroxy-7-dehydrocholesterol. Background technique [0002] Vitamin D3 is a steroid derivative that is important for bone formation. 25-hydroxy-7-dehydrocholesterol is an important raw material for the synthesis of 25-hydroxyvitamin D3. 25-hydroxyvitamin D3 is the active metabolite of vitamin D3 in animals and has stronger activity than vitamin D3. In addition to its ability to regulate calcium and phosphorus metabolism in the body, it is also widely used as a feed additive to promote bone development in avian animals. In addition, it can regulate the immune function of the human body and reduce the occurrence of osteoporosis, so its market prospect is very promising. As an important raw material of 25-hydroxyvitamin D3, 25-hydroxy-7-dehydrocholesterol is particularly important for its synthesis. [0003] The synthetic methods reported ...

Claims

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Application Information

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IPC IPC(8): C07J9/00C12P33/06C12P33/00
CPCC07J9/00C12P33/06C12P33/00Y02P20/55
Inventor 肖剑波
Owner 上海其正医药科技有限责任公司
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