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A synthetic method, the technology of drospirenone, applied in the field of organic synthesis, can solve problems such as side reactions, increased production costs, and expensive raw materials
Pending Publication Date: 2021-09-14
JIANGXI BAISIKANGRUI PHARMA +1
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[0003] In the prior art, high-pressure catalytic hydrogenation is often used in the preparation of drospirenone, which requires high technology and equipment, and the chromium reagent containing heavy metal chromium is use
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[0025] The invention provides a kind of synthetic method of drospirenone, comprising the following steps:
[0026] (1) metal lithium, 3-bromopropyl methyl ether and an aprotic organic solvent are mixed for an addition reaction to obtain an organolithium reagent;
[0027] (2) The organolithium reagent obtained in the step (1), the compound having the structure shown in formula II, and an aprotic organic solvent are mixed for a nucleophilic substitution reaction, and then mixed with an organic acid and water for a hydrolysis reaction to obtain A compound of the structure shown in formula III;
[0028]
[0029] (3) Mix the compound having the structure shown in the formula III obtained in the step (2) with a noble metal catalyst, persulfate, water and an aprotic organic solvent, and carry out oxidation reaction and lactonization reaction in sequence to obtain the compound having the formula IV Compounds of the structure shown;
[0030]
[0031] (4) Mixing the compound hav...
Embodiment 1
[0077] The synthetic method of drospirenone:
[0078] (1) Add 100mL of anhydrous tetrahydrofuran (THF) and 40mL of 3-bromopropyl methyl ether into a three-necked flask, pass through nitrogen for protection, and cool the reaction system to 0°C. Lithium metal, to avoid liquid splashing caused by too violent reaction, and then carry out addition reaction at 0°C for 1 h with stirring to obtain an organolithium reagent solution.
[0079] (2) The organolithium reagent solution obtained in (1), 10 g of 3β, 5β-dihydroxy-6β, 7β, 15β, 16β-dimethylene-pregnant-17-one (formula II) Compound with the structure shown) and 100mL of THF were mixed, and then the organolithium reagent solution obtained in the step (1) was added dropwise to the reaction system. After the addition was completed, the nucleophilic substitution reaction was carried out under stirring at room temperature for 5 to 8 hours. After TLC monitors that the reaction is completed, the reaction mixture solution is poured into ...
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Abstract
The invention provides a synthesis method of drospirenone, and belongs to the field of organic synthesis. The preparation method comprises the following steps: by taking a compound with a structure as shown in a formula II as an initial raw material, carrying out nucleophilic addition reaction on 17-site carbonyl of the compound and an organic lithium reagent, converting the carbonyl into hydroxyl, introducing propyl methyl ether, then carrying out hydrolysis reaction to obtain a compound with a structure as shown in a formula III, and then under the effect of a noble metal catalyst and persulfate, oxidizing hydroxy on third site into carbonyl, oxidizing hydroxyl on a 17alpha-site propyl group into an aldehyde group, carrying out aldol condensation to form a five-membered carboxylic acid lactone ring to obtain a compound with a structure as shown in a formula IV, and carrying out elimination reaction to obtain the compound drospirenone with a structure as shown in a formula I. The synthesis method provided by the invention has the advantages that most raw materials are cheap, high-pressure catalytic hydrogenation and use of a toxic chromium reagent are omitted, and drospirenone with the yield of 77% and the purity of 99.6% is prepared under mild reaction conditions.
Description
technical field [0001] The invention relates to the field of organic synthesis, in particular to a synthesis method of drospirenone. Background technique [0002] Drospirenone (Drospirenone), the chemical name is 6β, 7β, 15β, 16β-dimethylene-3-oxo-17α-pregna-4-ene-21,17-carboxylate, has anti-androgen And the role of anti-mineralocorticoids, is a high-efficiency, side effects of steroidal contraceptives. With the development of my country's economy and the improvement of people's living standards, contraceptive methods will also change accordingly. Among them, the market prospect of oral contraceptives is very broad, and drospirenone, as an excellent component of oral contraceptives, has a very large market potential. Development prospects. Therefore, it is of great significance to synthesize drospirenone in an economical and environmentally friendly manner. [0003] High-pressure catalytic hydrogenation is often used in the preparation of drospirenone in the prior art, whi...
Claims
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