Gacyclidine, GK-11
1-((1R,2S)-2-甲基-1-(硫吩-2-基)环己基)吡哌啶Chemical Name: cis-1-[2-Methyl-1-(2-thienyl)cyclohexyl]piperidine
CAS No. 68134-81-6
项目整合开发状态: Phase II
项目研究机构: CNRS (Originator), INSERM (Originator), Ipsen (Originator)
合成路线:The condensation of 2-methylcyclohexanone (I) with 2-thienyl lithium (II) or 2-thienylmagnesium bromide (III) gives cyclohexanol (IV) as a diastereomeric mixture,which was treated with Na-N3 in trichloroacetic acid to yield the azide (V).The reduction of (V) with LiAlH4 or RaNi/iPr-OH affords the corresponding amine (VI),preferentially with the cis-configuration.Finally,this compound is condensed with 1,5-dibromopentane (VII) by means of K2CO3 in acetonitrile to provide the target compound as a diastereomeric mixture.The separation of the cis- and trans- racemates has been performed by HPLC.The optical resolution was performed by a cumbersome crystallization process using CSA and di-p-toluoyltartaric acid.
📌 参考资料/链接：
参考文献标题:Pharmaceutical compsns.for neuroprotection containing arylcyclohexylamines
文献作者:Kamenka,J.-M.; Privat,A.; Chicheportiche,R.; Rondouin,G.(CNRS (Centre National de la Recherche Scientifique))
参考来源:US 5179109; WO 9005524
📄 详细内容
合成路线:The condensation of 2-methylcyclohexanone (I) with 2-thienyl lithium (II) or 2-thienylmagnesium bromide (III) gives cyclohexanol (IV) as a diastereomeric mixture,which was treated with Na-N3 in trichloroacetic acid to yield the azide (V).The reduction of (V) with LiAlH4 or RaNi/iPr-OH affords the corresponding amine (VI),preferentially with the cis-configuration.Finally,this compound is condensed with 1,5-dibromopentane (VII) by means of K2CO3 in acetonitrile to provide the target compound as a diastereomeric mixture.The separation of the cis- and trans- racemates has been performed by HPLC.The optical resolution was performed by a cumbersome crystallization process using CSA and di-p-toluoyltartaric acid.
参考文献标题:Homochiral structures derived from 1-[1-(2-thienyl)cyclohexyl]piperidine (TCP) are potent non-competitive antagonists of glutamate at NMDA receptor sites
文献作者:Michaud,M.; et al.
参考来源:Eur J Med Chem 1994,29(11),869
产品链接: CAS No. 68134-81-6››