434-03-7Relevant articles and documents
A Short and Efficient Synthetic Method for the Corticosteroid Side-Chain from 17-Keto Steroids
Kataoka, Hideaki,Watanabe, Kiyoshi,Miyazaki, Ken-ichi,Tahara, Shin-ichiro,Ogu, Ken-ichi,et al.
, p. 1705 - 1708 (1990)
21-Acyloxy-16(17)-ene-20-keto steroids were synthesized from 17-keto steroids in 4 steps using palladium(II)-catalyzed oxidative rearrangement of propargyl esters as a key reaction.
Method for preparing 17alpha-hydroxyprogesterone
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Paragraph 0028; 0030, (2017/08/27)
The invention discloses a method for preparing 17alpha-hydroxyprogesterone. According to the method, 4-androstenedione I serves as the raw material, a 17-site branched chain is introduced through ethynylation reaction, a 17-site beta-hydroxyl group is converted into an alpha-hydroxyl group through catalytic reaction, and finally 17alpha-hydroxyprogesterone is prepared through carbonylation reaction. The reaction formula is shown in the description. Four steps of reaction are conducted with 4-androstenedione as the raw material, a 17-site side chain is introduced through ethynylation reaction, the 17beta-hydroxyl group is converted into the 17alpha-hydroxyl group through transposition reaction, the weight yield of each step ranges from 85% to 109%, the total weigh yield is 85% or above, use of virulent acetone cyanohydrin is avoided, the raw material conversion rate is high, selectivity is good, production cost of 17alpha-hydroxyprogesterone is reduced, the process is safe, and large-scale industrial production is easy.
Process for the preparation of danazol
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, (2019/02/04)
The invention discloses preparation methods of danazol and an intermediate thereof. The preparation method of danazol is prepared by the steps of taking androstenedione as a starting raw material, and carrying out 3-site enol etherification, 17-site carbonyl ethinylation, 3-site hydrolysis, 2-site methylidynel hydroxylation and oximation to obtain danazol. The 3-site enol etherification comprises firstly carrying out a reaction of androstenedione and triethyl orthoformate for 4-10 h in the presence of absolute ethyl alcohol and p-toluenesulfonic acid and at the temperature of 30-50 DEG C, then adding triethylamine at the temperature of 0-10 DEG C, and continuing to carry out a reaction for 0.2-1 h; the 17-site carbonyl ethinylation comprises firstly carrying out a reaction of a potassium hydroxide powder for 1-2 h in an acetylene airflow and at the temperature of 5-10 DEG C, and then carrying out a reaction with the 3-site enol etherified product for 2-4 h in the presence of tetrahydrofuran and a catalyst, at the temperature of 15-30 DEG C and in the acetylene airflow. The 3-site enol etherification is mild in reaction conditions and relatively high in yield, and the 17-site carbonyl ethynylation is relatively high in reaction yield and relatively short in time.