Synthesis of N-[4-(2'-[18F]fluoroalkoxybenzoyl)]- And N-(3-[123I]iodo-4-methoxybenzoyl)pyrrolidin-2-ones as potential brain imaging agents

Research output: Contribution to journalArticle

Abstract

– The microfluidic synthesis of promising brain imaging PET agents N-[4-(2’-[18F]fluoroalkyloxybenzoyl)]pyrrolidin-2-ones 13a-c was accomplished by nucleophilic radiofluorination of the corresponding tosylate precursors 9a-c with Kryptofix-potassium carbonate-[18F]fluoride. Decay corrected radiochemical yields of 35±5% (13a), 38±8% (13b) and 40±5% (13c) were obtained with radiochemical purities of ≥ 93%. The total reaction time, including HPLC purification was 40 min. N-(3-[123I]Iodo-4-methoxybenzoyl)pyrrolidin-2-one, 18, was prepared by radioiododestannylation of tin precursor 17 using Na123I and 0.3% peracetic acid in 84% radiochemical yield in 20 min.

Original languageEnglish (US)
Pages (from-to)1226-1236
Number of pages11
JournalHeterocycles
Volume97
Issue number2
DOIs
StatePublished - Jan 1 2018

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Peracetic Acid
Microfluidics
Tin
Fluorides
Neuroimaging
Purification
Brain
High Pressure Liquid Chromatography
Imaging techniques
potassium carbonate

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

@article{0038e36aeba943b1ab5c69ad6b8b7ee6,
title = "Synthesis of N-[4-(2'-[18F]fluoroalkoxybenzoyl)]- And N-(3-[123I]iodo-4-methoxybenzoyl)pyrrolidin-2-ones as potential brain imaging agents",
abstract = "– The microfluidic synthesis of promising brain imaging PET agents N-[4-(2’-[18F]fluoroalkyloxybenzoyl)]pyrrolidin-2-ones 13a-c was accomplished by nucleophilic radiofluorination of the corresponding tosylate precursors 9a-c with Kryptofix-potassium carbonate-[18F]fluoride. Decay corrected radiochemical yields of 35±5{\%} (13a), 38±8{\%} (13b) and 40±5{\%} (13c) were obtained with radiochemical purities of ≥ 93{\%}. The total reaction time, including HPLC purification was 40 min. N-(3-[123I]Iodo-4-methoxybenzoyl)pyrrolidin-2-one, 18, was prepared by radioiododestannylation of tin precursor 17 using Na123I and 0.3{\%} peracetic acid in 84{\%} radiochemical yield in 20 min.",
author = "Murthy Akula and David Blevins and Kabalka, {George W.} and Dustin Osborne",
year = "2018",
month = "1",
day = "1",
doi = "10.3987/COM-18-S(T)75",
language = "English (US)",
volume = "97",
pages = "1226--1236",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",
number = "2",

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TY - JOUR

T1 - Synthesis of N-[4-(2'-[18F]fluoroalkoxybenzoyl)]- And N-(3-[123I]iodo-4-methoxybenzoyl)pyrrolidin-2-ones as potential brain imaging agents

AU - Akula, Murthy

AU - Blevins, David

AU - Kabalka, George W.

AU - Osborne, Dustin

PY - 2018/1/1

Y1 - 2018/1/1

N2 - – The microfluidic synthesis of promising brain imaging PET agents N-[4-(2’-[18F]fluoroalkyloxybenzoyl)]pyrrolidin-2-ones 13a-c was accomplished by nucleophilic radiofluorination of the corresponding tosylate precursors 9a-c with Kryptofix-potassium carbonate-[18F]fluoride. Decay corrected radiochemical yields of 35±5% (13a), 38±8% (13b) and 40±5% (13c) were obtained with radiochemical purities of ≥ 93%. The total reaction time, including HPLC purification was 40 min. N-(3-[123I]Iodo-4-methoxybenzoyl)pyrrolidin-2-one, 18, was prepared by radioiododestannylation of tin precursor 17 using Na123I and 0.3% peracetic acid in 84% radiochemical yield in 20 min.

AB - – The microfluidic synthesis of promising brain imaging PET agents N-[4-(2’-[18F]fluoroalkyloxybenzoyl)]pyrrolidin-2-ones 13a-c was accomplished by nucleophilic radiofluorination of the corresponding tosylate precursors 9a-c with Kryptofix-potassium carbonate-[18F]fluoride. Decay corrected radiochemical yields of 35±5% (13a), 38±8% (13b) and 40±5% (13c) were obtained with radiochemical purities of ≥ 93%. The total reaction time, including HPLC purification was 40 min. N-(3-[123I]Iodo-4-methoxybenzoyl)pyrrolidin-2-one, 18, was prepared by radioiododestannylation of tin precursor 17 using Na123I and 0.3% peracetic acid in 84% radiochemical yield in 20 min.

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