PE2I
8-氮杂双环[3.2.1]辛烷-2-羧酸,8-[(2E)-3-碘-2-丙烯-1-基]-3-(4-甲基苯基)-,甲基酯,(1R,2S,3S,5S)-Chemical Name: (1R,2S,3S,5S)-8-[3-Iodo-2(E)-propenyl]-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester
CAS No. 188680-71-9, 209670-90-6 ([123I]-labeled), 199734-14-0 (125I-labeled), 311767-40-5 (labeled)
项目整合开发状态: Clinical
项目研究机构: CIS Bio International (Originator)
合成路线:Conjugate addition of tolylmagnesium bromide (II) to ecgonidine methyl ester (I) provided the 3-beta-tolyl tropane derivative (III).N-Dealkylation of (III) to produce the nortropane analogue (V) was carried out via acylation with trichloroethyl chloroformate,followed by reductive cleavage of the resultant trichloroethyl carbamate (IV) with Zn and HOAc.Alkylation of the secondary amine (V) with propargyl bromide (VI) afforded the corresponding propargyl amine (VII).Subsequent hydrostannylation of the propargyl group furnished the desired (E)-stannylpropenyl compound (VIII) along with the corresponding (Z)-isomer.In an improved procedure,amine (V) was alkylated with (E)-3-chloro-1-(tributylstannyl)-1-propene (IX) to yield pure (VIII).Finally,the title vinyl iodide was obtained by iododestannylation of (VIII) employing iodine in cold CHCl3.
📌 参考资料/链接：
参考文献标题:Tropane derivs.useable in particular for in vivo detection of dopamine transporters
文献作者:Mauclaire,L.; Edmond,P.; Guilloteau,D.; Besnard,J.-C.; Frangin,Y.(CIS Bio International)
参考来源:EP 0901491; JP 2000510141; US 6180083; WO 9743285
📄 详细内容
合成路线:Conjugate addition of tolylmagnesium bromide (II) to ecgonidine methyl ester (I) provided the 3-beta-tolyl tropane derivative (III).N-Dealkylation of (III) to produce the nortropane analogue (V) was carried out via acylation with trichloroethyl chloroformate,followed by reductive cleavage of the resultant trichloroethyl carbamate (IV) with Zn and HOAc.Alkylation of the secondary amine (V) with propargyl bromide (VI) afforded the corresponding propargyl amine (VII).Subsequent hydrostannylation of the propargyl group furnished the desired (E)-stannylpropenyl compound (VIII) along with the corresponding (Z)-isomer.In an improved procedure,amine (V) was alkylated with (E)-3-chloro-1-(tributylstannyl)-1-propene (IX) to yield pure (VIII).Finally,the title vinyl iodide was obtained by iododestannylation of (VIII) employing iodine in cold CHCl3.
参考文献标题:Synthesis and ligand bindin of nortropane derivatives: N-substituted 2beta-carbomethoxy-3beta-(4'-iodophenyl)nortropane and N-(3-iodotrop-(2E)-enyl)-2beta-carbomethoxy-3beta-(3',4'-disubstituted phenyl)nortropane.New high-affinity and selective compounds
文献作者:Emond,P.; Garreau,L.; Chalon,S.; Boazi,M.; Caillet,M.; Bricard,J.; Frangin,Y.; Mauclaire,L.; Besnard,J.C.; Guilloteau,D.
参考来源:J Med Chem 1997,40(9),1366
合成路线:The reaction of the tributystannyl derivative (I) with 123INa and H2O2 in ethanol yields the target radiolabelled compound.
参考文献标题:New preparation of [123I]PE2I: Investigation of the oxidation and purification steps
文献作者:Berthommier,E.; et al.
参考来源:J.Label.Comp.and Radiopharm.2002,45(12),1019
产品链接: CAS No. 188680-71-9›› 产品链接: CAS No.199734-14-0››