新产品编号:1297749

Chemical Name: (+)-cis-4-Methyl-5-pentylpyrrolidin-2-imine hydrochloride
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator)
合成路线:Michael addition of 1-nitrohexane (I) to methyl crotonate (II) provided nitroester (III) as a mixture of diastereoisomers.Reduction and cyclization of (III) by hydrogenation over Raney Nickel gave the cis- (IV) and trans- (V) pyrrolidinones,which were separated by column chromatography.Racemic cis isomer (IV) was resolved upon condensation with (R)-(+)-1-naphythylethyl isocyanate (VI) in boiling benzene,followed by chromatographic separation of the resulting diastereomeric mixture of ureides.The desired isomer (VII) was then hydrolyzed with sodium butoxide in refluxing n-BuOH to furnish the (+)-cis pyrrolidinone (+)(IV).Subsequent treatment with trimethyloxonium tetrafluoborate produced the iminoether (VIII),which was finally reacted with NH4Cl in refluxing MeOH to provide the corresponding iminopyrrolidine.