Tributylvinyltin → 2beta-Carbomethoxy-3beta-(4'-ethenylphenyl)tropane
Reaction equation
[C:1]([C@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)[CH2:10][C@H:9]2[N:19]([CH3:20])[C@@H:6]1[CH2:7][CH2:8]2)([O:3][CH3:4])=[O:2].[CH:21]([Sn](CCCC)(CCCC)CCCC)=[CH2:22]>>[C:1]([C@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([CH:21]=[CH2:22])=[CH:14][CH:13]=2)[CH2:10][C@H:9]2[N:19]([CH3:20])[C@@H:6]1[CH2:7][CH2:8]2)([O:3][CH3:4])=[O:2]Participants
3
Procedure
Scheme 5 provides exemplary synthetic route for 2β-carbomethoxy-3β-4′-(Z-2-iodoethenyl)phenyl)tropane (ZIET) and [123I] ZIET. The preparation of ZIET involved a five-step sequence of reactions. In this synthetic approach 2β-carbomethoxy-3β-(4′-bromophenyl)tropane was treated with vinyltributyltin to yield 2β-carbomethoxy -3β-(4′-ethenylphenyl)tropane. The vinyltropane derivative was converted to 2β-carbomethoxy-3β-(4′-formylphenyl)tropane followed by reaction with triphenyl-phosphoniumiodomethyne yllide to give ZIET.