A new nucleophilic fluorine-18 labeling method for aliphatic mesylates: reaction in ionic liquids shows tolerance for water.

Abstract:

:[see text for equation] Nucleophilic [(18)F]fluorination of some halo- and mesyloxyalkanes to the corresponding [(18)F]fluoroalkanes with fluoride-18 obtained from an (18)O(p,n) [(18)F]F reaction, using an ionic liquid as a reaction medium, has been studied as a new method for fluorine-18 labeling. Of the various ionic liquids, 1-butyl-3-methylimidazolium triflate ([bmim][OTf]) in the presence of Cs(2)CO(3), gave the highest radiochemical yields. This method is rapid and particularly convenient because [(18)F]fluoride in H(2)O can be added directly to the reaction media, obviating the careful drying that is typically required for currently used radiofluorination methods. As a model reaction, [(18)F]fluorination of 2-(3-methanesulfonyloxypropoxy)naphthalene was found to provide the corresponding [(18)F]fluoro product in 93+/-1.2% (n=3) radiochemical yield, after reaction at 120 (o)C for 5-10 min under optimized conditions. Thus, we anticipate that this method will be very useful in the labeling of various molecules with [(18)F]fluoride in a convenient manner.

journal_name

Nucl Med Biol

authors

Kim DW,Choe YS,Chi DY

doi

10.1016/s0969-8051(03)00017-9

keywords:

subject

Has Abstract

pub_date

2003-05-01 00:00:00

pages

345-50

issue

4

eissn

0969-8051

issn

1872-9614

pii

S0969805103000179

journal_volume

30

pub_type

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