SB-380732

Chemical Name: cis-3-(3,4-Dichlorophenyl)-N-[4-[exo-3-(5-hydroxy-1H-indol-3-yl)-8-azabicyclo[3.2.1]oct-8-ylmethyl]cyclohexyl]-2-propenamide
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:Protection of cis-4-aminocyclohexanecarboxylic acid (I) with di-tert-butyl dicarbonate provided the N-Boc-amino acid (II).After conversion of (II) to the mixed anhydride (III) with methyl chloroformate,reduction with NaBH4 afforded alcohol (IV).Subsequent Swern oxidation of alcohol (IV) gave aldehyde (V).This was then subjected to reductive amination with the indolyl tropane (VI) in the presence of NaBH(OAc)3 to furnish the tertiary amine (VII).Removal of the Boc protecting group of (VII) with ethanolic HCl,followed by coupling of the resulting amine (VIII) with 3,4-dichlorocinnamic acid,yielded the target amide.