Y-39241
Chemical Name: N-[1-[2-(4-Fluorophenyl)ethyl]pyrrolidin-3(S)-yl]adamantane-1-carboxamide hydrochloride hydrate
CAS No. 267643-59-4 (anhydrous, free base)
项目整合开发状态: Preclinical
项目研究机构: Mitsubishi Pharma (Originator)
合成路线:Condensation of (S)-3-amino-1-benzylpyrrolidine (I) with 1-adamantanecarbonyl chloride (II) by means of Et3N in dichloromethane affords amide (III),which is then debenzylated by hydrogenolysis over Pd/C and hydrazine monohydrate to provide amine (IV).Subsequent N-alkylation of (IV) with tosylate (V) in acetonitrile in the presence of K2CO3 furnishes the corresponding alylated compound (VI),which is finally converted into the desired hydrochloride monohydrate derivative by first treatment with HCl:isopropanol in ethyl acetate followed by recrystallization in EtOH:H2O using activated carbon.
📌 参考资料/链接：
参考文献标题:Pyrrolidine cpds.and medicinal utilization thereof
文献作者:Kuroita,T.; Nakagawa,H.; Fujio,M.(Welfide Corporation)
参考来源:EP 1125922; WO 0026186
📄 详细内容
合成路线:Condensation of (S)-3-amino-1-benzylpyrrolidine (I) with 1-adamantanecarbonyl chloride (II) by means of Et3N in dichloromethane affords amide (III),which is then debenzylated by hydrogenolysis over Pd/C and hydrazine monohydrate to provide amine (IV).Subsequent N-alkylation of (IV) with tosylate (V) in acetonitrile in the presence of K2CO3 furnishes the corresponding alylated compound (VI),which is finally converted into the desired hydrochloride monohydrate derivative by first treatment with HCl:isopropanol in ethyl acetate followed by recrystallization in EtOH:H2O using activated carbon.
参考文献标题:N-[1-(2-phenylethyl)pyrrolidin-3-yl]-1-adamantanecarboxamides as novel 5-HT2 receptor antagonists
文献作者:Fujio,M.; Kuroita,T.; Sakai,Y.; Nakagawa,H.; Matsumoto,Y.
参考来源:Bioorg Med Chem Lett 2000,10(21),2457