Altropane, IACFT, Altropane
(1R,2S,3S,5S)-3-(4-氟苯基)-8-[(E)-3-碘丙-2-烯基]-8-氮杂双环[3.2.1]辛烷-2-羧酸甲酯Chemical Name: (1R,2S,3S,5S)-3-(4-Fluorophenyl)-8-[3-iodo-2(E)-propenyl]-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester
CAS No. 180468-34-2, 208517-65-1 ([123I]-labeled), 180268-78-4 ([125I]-isotope)
项目整合开发状态: Phase III
项目研究机构: MDS Nordion (Supplier), Organix (Originator), Boston Life Sciences (Licensee)
合成路线:Addition of tributyltin hydride to the triple bond of propargyl alcohol (I) in the presence of AIBN provided a mixture of (Z)-(II) and (E)-3-(tributylstannyl)-2-propen-1-ol (III),which were separated by column chromatography.The desired (E)-allyl alcohol (III) was further converted to the corresponding chloride (IV) by treatment with PPh3 in refluxing CCl4.Alkylation of the nortropane derivative (V) with chloride (IV) in the presence of celite-supported KF furnished the N-(tributylstannyl)propenyl nortropane (VI).The target iodinated compound was then prepared by treatment of (VI) with N-iodosuccinimide.
📌 参考资料/链接：
参考文献标题:Substd.2-carboxyalkyl-3-(fluorophenyl)-8-(3-haloprofen-2-yl) nortropanes and their use as imaging agents for neurodegenerative disorders
文献作者:Elmaleh,D.R.; Madras,B.K.; Meltzer,P.; Hanson,R.N.(General Hospital Corporation; Harvard College; Northeastern University)
参考来源:EP 0734385; EP 1081147; WO 9511901
📄 详细内容
合成路线:Addition of tributyltin hydride to the triple bond of propargyl alcohol (I) in the presence of AIBN provided a mixture of (Z)-(II) and (E)-3-(tributylstannyl)-2-propen-1-ol (III),which were separated by column chromatography.The desired (E)-allyl alcohol (III) was further converted to the corresponding chloride (IV) by treatment with PPh3 in refluxing CCl4.Alkylation of the nortropane derivative (V) with chloride (IV) in the presence of celite-supported KF furnished the N-(tributylstannyl)propenyl nortropane (VI).The target iodinated compound was then prepared by treatment of (VI) with N-iodosuccinimide.
参考文献标题:Preparation and biological evaluation of iodine-125-IACFT: A selective SPECT agent for imaging dopamine transporter sites
文献作者:Elmaleh,D.R.; Fischman,A.J.; Shoup,T.M.; Byon,C.; Hanson,R.N.; Liang,A.Y.; Meltzer,P.C.; Madras,B.K.
参考来源:J Nucl Med 1996,37(7),1197