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ChemicalBook CAS DataBase List Norethindrone
68-22-4

Norethindrone synthesis

10synthesis methods
Norethindrone, 17α-ethynyl-17β-hydroxyestra-4-en-4-one (28.3.12), is made from 19-nor-4-androsten-3,17-dione (28.3.10), which is in turn synthesized by partial reduction of the aromatic region of the 3-O-methyl ether of estrone with lithium in liquid ammonia, and simultaneously of the keto-group at C17 to and hydroxyl group, which is then oxidized back to a keto-group by chromium (VI) oxide in acetic acid. The conjugated with the double bond carbonyl group at C3 is then transformed to dienol ethyl ether (28.3.11) using ethyl orthoformate. The obtained product is ethynylated by acetylene in the presence of potassium tert-butoxide. After hydrochloric acid hydrolysis, of the formed O-potassium derivative, during which the enol ether is also hydrolyzed, and the remaining double bond is shifted, the desired norethindrone (28.3.12) is obtained.

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Yield:68-22-4 100%

Reaction Conditions:

Stage #1:estra-4-ene-3,17-dione with potassium hydroxide in toluene;tert-butyl alcohol under 760.051 Torr; for 0.166667 h;Reflux;Industrial scale;
Stage #2:acetylene in tert-butyl methyl ether;toluene for 6 h;Industrial scale;

Steps:

1.1 Alkylation reaction:
800kg toluene, 20kg potassium hydroxide, 40kg tert-butanol at normal pressure and reflux dehydration for 2 hours, lower the temperature to 30°C, add 100kg acid decarboxylate (I) dissolved in 200kg toluene, and stir for 10 minutes. Acetylene gas was introduced. After 6 hours of ventilation, TLC detection was started. TLC analysis of the raw material reaction was complete. The ventilation was stopped, 200kg of water was added to quench and wash, and the layers were separated. Concentrate under reduced pressure, add 100kg of ethanol, discharge, and dry to obtain 100kg of norethindrone (II), with a mass yield of 100%, detection HPLC ≥99%, single impurity ≤0.5%.

References:

Zhejiang Xianju Junye Pharmaceutical Co., Ltd.;Jiangxi Junye Bio-pharmaceutical Co., Ltd.;Xu Sihu;Zhang Zhengbin;Chen Yinghui;Li Chun;Wu Xiaokai;Pan Baofeng CN110981930, 2020, A Location in patent:Paragraph 0028-0031

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