(-)-cis-MR-22, (-)-MR-22
Chemical Name: (-)-cis-2-[N-(1-Adamantyl)-N-methylaminomethyl]-1-phenylcyclopropanecarboxylic acid methyl ester
CAS No. 290342-29-9
项目整合开发状态: Preclinical
项目研究机构: Universit?degli Studi di Catania (Originator), Universit?degli Studi di Messina (Originator)
合成路线:Opening of the known lactone (I) with HBr in HOAc produces the racemic cis bromo-acid (II).Acid (II) is then converted to the corresponding methyl ester (III) by chlorination with SOCl2,followed by treatment with methanolic HCl.Acylation of 1-adamantanamine (IV) with ethyl formate yields the formamide (V),which is subsequently reduced to the N-methyl amine (VI) employing LiAlH4 in THF.Finally,alkylation of the secondary amine (VI) with bromo ester (III) in the presence of NaHCO3 in hot DMF gives rise to the title compound.
📌 参考资料/链接：
参考文献标题:Substituted 1-phenyl-2-cyclopropylmethylamines with high affinity and selectively for sigma sites
文献作者:Ronsisvalle,G.; Marrazzo,A.; Prezzavento,O.; Pasquinucci,L.; Falcucci,B.; Di Toro,R.D.; Spampinato,S.
参考来源:Bioorg Med Chem 2000,8(6),1503
📄 详细内容
合成路线:In a closely related method,bromo-ester (I) is condensed with 1-adamantanamine (II) in hot DMF to afford amino ester (III).The secondary amine of (III) is then alkylated with iodomethane to produce the title compound.
参考文献标题:Synthesis of (+)- and (-)-cis-2-[(1-adamantylamino)-methyl]-1-phenylcyclopropane derivatives as high affinity probes for sigma1 and sigma2 binding sites
文献作者:Marrazzo,A.; Prezzavento,O.; Pappalardo,M.S.; Bousquet,E.; Iadanza,M.; Pike,V.W.; Ronsisvalle,G.
参考来源:Farmaco 2002,57(1),45