Etonogestrel, Org-3236
依托孕烯Chemical Name: (17alpha)-13-Ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one; 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one-17-ol; 11-Methylene-17alpha-ethynyl-17beta-hydroxy-18-methyl-DELTA4-estren-3-one
CAS No. 54048-10-1
项目整合开发状态: Launched
项目研究机构: Organon (Originator)
合成路线:The ketalization of 11alpha-hydroxy-18-methyl-DELTA4-estrene-3,17-dione (I) with ethylene glycol (A) by means of ethyl orthoformate and p-toluene sulfonic acid gives the diketal (II),which is oxidized with CrO3 in acetone yielding the ketone (III).The Wittig reaction of (III) with triphenylmethyl-phosphonium bromide (B) by means of NaH in benzene-DMSO affords 11-methylene-18-methyl-DELTA4-estren-3,17-dione diethyleneketal (IV),which is hydrolyzed with HCl in acetone to the diketone (V).The reaction of (V) with pyrrolidine (C) in methanol gives the N-pyrrolidinyl derivative (VI),which is condensed with potassium acetylide (D) in THF yielding 17alpha-ethynyl derivative (VII).Finally,this compound is hydrolyzed with acetic acid in methanol - water.
📌 参考资料/链接：
参考文献标题:ORG-3236
文献作者:Hillier,K.; Castar,J.
参考来源:Drugs Fut 1978,3(9),664
📄 详细内容
合成路线:The ketalization of 11alpha-hydroxy-18-methyl-DELTA4-estrene-3,17-dione (I) with ethylene glycol (A) by means of ethyl orthoformate and p-toluene sulfonic acid gives the diketal (II),which is oxidized with CrO3 in acetone yielding the ketone (III).The Wittig reaction of (III) with triphenylmethyl-phosphonium bromide (B) by means of NaH in benzene-DMSO affords 11-methylene-18-methyl-DELTA4-estren-3,17-dione diethyleneketal (IV),which is hydrolyzed with HCl in acetone to the diketone (V).The reaction of (V) with pyrrolidine (C) in methanol gives the N-pyrrolidinyl derivative (VI),which is condensed with potassium acetylide (D) in THF yielding 17alpha-ethynyl derivative (VII).Finally,this compound is hydrolyzed with acetic acid in methanol - water.
参考文献标题:Novel 11,11-alkylidene steroids
文献作者:Van den Broek,A.J.
参考来源:DE 2361120; ES 421253; FR 2209577; GB 1455270; JP 50029548; US 3927046
产品链接: CAS No. 54048-10-1››