Tributylvinyltin → 2beta-Carbomethoxy-3beta-(4'-ethenylphenyl)tropane

HRID 1760500Notes

Reaction equation

HRID 1760500 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

Reactant 2

HCID 81998TributylvinyltinHCID 57340111Methyl (1R,2S,3S,5S)-3-(4-bromophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Product 1

HCID 107555722beta-Carbomethoxy-3beta-(4'-ethenylphenyl)tropane

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.

Workup

  1. customThe preparation of ZIET

Sources & evidence

ORD record
ord-4e4e63963dc54c48bf6226fb64be5562
Source dataset
uspto-grants-2005_01
Patent number
US06843979B2

Reaction notes

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