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

Dong Wook Kim; Yearn Seong Choe; Dae Yoon Chi

doi:10.1016/S0969-8051(03)00017-9

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

Dong Wook Kim, Yearn Seong Choe, Dae Yoon Chi

Research output: Contribution to journal › Article › peer-review

77 Scopus citations

Abstract

Nucleophilic [¹⁸F]fluorination of some halo- and mesyloxyalkanes to the corresponding [¹⁸F]fluoroalkanes with fluoride-18 obtained from an ¹⁸O(p,n) [¹⁸F]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 Cs₂CO₃, gave the highest radiochemical yields. This method is rapid and particularly convenient because [¹⁸F]fluoride in H₂O 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, [¹⁸F]fluorination of 2-(3-methanesulfonyloxypropoxy)naphthalene [1] was found to provide the corresponding [¹⁸F]fluoro product in 93±1.2% (n=3) radiochemical yield, after reaction at 120°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 [¹⁸F]fluoride in a convenient manner.

Original language	English
Pages (from-to)	345-350
Number of pages	6
Journal	Nuclear Medicine and Biology
Volume	30
Issue number	4
DOIs	https://doi.org/10.1016/S0969-8051(03)00017-9
State	Published - May 2003

Bibliographical note

Funding Information:
This research was supported by the Korea Science and Engineering Fund (No 97-03-01-01-5-L) and the National Research Laboratory Program. We thank Prof. John A. Katzenellenbogen for comments on this manuscript.

Keywords

Fluorination
Fluorine-18
Ionic liquid
Labeling method
PET
Potassium fluoride

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/S0969-8051(03)00017-9

Cite this

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title = "A new nucleophilic fluorine-18 labeling method for aliphatic mesylates: Reaction in ionic liquids shows tolerance for water",

abstract = "Nucleophilic [18F]fluorination of some halo- and mesyloxyalkanes to the corresponding [18F]fluoroalkanes with fluoride-18 obtained from an 18O(p,n) [18F]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 Cs2CO3, gave the highest radiochemical yields. This method is rapid and particularly convenient because [18F]fluoride in H2O 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, [18F]fluorination of 2-(3-methanesulfonyloxypropoxy)naphthalene [1] was found to provide the corresponding [18F]fluoro product in 93±1.2% (n=3) radiochemical yield, after reaction at 120°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 [18F]fluoride in a convenient manner.",

keywords = "Fluorination, Fluorine-18, Ionic liquid, Labeling method, PET, Potassium fluoride",

author = "Kim, {Dong Wook} and Choe, {Yearn Seong} and Chi, {Dae Yoon}",

note = "Funding Information: This research was supported by the Korea Science and Engineering Fund (No 97-03-01-01-5-L) and the National Research Laboratory Program. We thank Prof. John A. Katzenellenbogen for comments on this manuscript. ",

year = "2003",

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TY - JOUR

T1 - A new nucleophilic fluorine-18 labeling method for aliphatic mesylates

T2 - Reaction in ionic liquids shows tolerance for water

AU - Kim, Dong Wook

AU - Choe, Yearn Seong

AU - Chi, Dae Yoon

N1 - Funding Information: This research was supported by the Korea Science and Engineering Fund (No 97-03-01-01-5-L) and the National Research Laboratory Program. We thank Prof. John A. Katzenellenbogen for comments on this manuscript.

PY - 2003/5

Y1 - 2003/5

N2 - Nucleophilic [18F]fluorination of some halo- and mesyloxyalkanes to the corresponding [18F]fluoroalkanes with fluoride-18 obtained from an 18O(p,n) [18F]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 Cs2CO3, gave the highest radiochemical yields. This method is rapid and particularly convenient because [18F]fluoride in H2O 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, [18F]fluorination of 2-(3-methanesulfonyloxypropoxy)naphthalene [1] was found to provide the corresponding [18F]fluoro product in 93±1.2% (n=3) radiochemical yield, after reaction at 120°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 [18F]fluoride in a convenient manner.

AB - Nucleophilic [18F]fluorination of some halo- and mesyloxyalkanes to the corresponding [18F]fluoroalkanes with fluoride-18 obtained from an 18O(p,n) [18F]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 Cs2CO3, gave the highest radiochemical yields. This method is rapid and particularly convenient because [18F]fluoride in H2O 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, [18F]fluorination of 2-(3-methanesulfonyloxypropoxy)naphthalene [1] was found to provide the corresponding [18F]fluoro product in 93±1.2% (n=3) radiochemical yield, after reaction at 120°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 [18F]fluoride in a convenient manner.

KW - Fluorination

KW - Fluorine-18

KW - Ionic liquid

KW - Labeling method

KW - PET

KW - Potassium fluoride

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

Abstract

Bibliographical note

Keywords

UN SDGs

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