Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-11C]acetic acid

Sojeong Lee; David L. Alexoff; Colleen Shea; Dohyun Kim; Michael Schueller; Joanna S. Fowler; Wenchao Qu

doi:10.1016/j.tetlet.2014.12.014

Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-¹¹C]acetic acid

Sojeong Lee
, David L. Alexoff
, Colleen Shea
, Dohyun Kim
, Michael Schueller
, Joanna S. Fowler
, Wenchao Qu

Psychiatry

Brookhaven National Laboratory
Stony Brook University

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

8 Scopus citations

Abstract

An operationally friendly, two-step, one-pot process has been developed for the rapid synthesis of carbon-11 labeled indole-3-acetic acid ([¹¹C]IAA or [¹¹C]auxin). By replacing an aprotic polar solvent with tetraethylene glycol, nucleophilic [¹¹C]cyanation and alkaline hydrolysis reactions were performed consecutively in a single pot without a time-consuming intermediate purification step. The entire production time for this updated procedure is 55 min, which dramatically simplifies the entire synthesis and reduces the starting radioactivity required for a whole plant imaging study.

Original language	English
Pages (from-to)	517-520
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	3
DOIs	https://doi.org/10.1016/j.tetlet.2014.12.014
State	Published - Jan 14 2015

Keywords

Carbon-11 labeled indole-3-acetic acid
Nucleophilic [C]cyanation
Tetraethylene glycol
Two-step one-pot

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10.1016/j.tetlet.2014.12.014

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title = "Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-11C]acetic acid",

abstract = "An operationally friendly, two-step, one-pot process has been developed for the rapid synthesis of carbon-11 labeled indole-3-acetic acid ([11C]IAA or [11C]auxin). By replacing an aprotic polar solvent with tetraethylene glycol, nucleophilic [11C]cyanation and alkaline hydrolysis reactions were performed consecutively in a single pot without a time-consuming intermediate purification step. The entire production time for this updated procedure is 55 min, which dramatically simplifies the entire synthesis and reduces the starting radioactivity required for a whole plant imaging study.",

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AU - Lee, Sojeong

AU - Alexoff, David L.

AU - Shea, Colleen

AU - Kim, Dohyun

AU - Schueller, Michael

AU - Fowler, Joanna S.

AU - Qu, Wenchao

PY - 2015/1/14

Y1 - 2015/1/14

N2 - An operationally friendly, two-step, one-pot process has been developed for the rapid synthesis of carbon-11 labeled indole-3-acetic acid ([11C]IAA or [11C]auxin). By replacing an aprotic polar solvent with tetraethylene glycol, nucleophilic [11C]cyanation and alkaline hydrolysis reactions were performed consecutively in a single pot without a time-consuming intermediate purification step. The entire production time for this updated procedure is 55 min, which dramatically simplifies the entire synthesis and reduces the starting radioactivity required for a whole plant imaging study.

AB - An operationally friendly, two-step, one-pot process has been developed for the rapid synthesis of carbon-11 labeled indole-3-acetic acid ([11C]IAA or [11C]auxin). By replacing an aprotic polar solvent with tetraethylene glycol, nucleophilic [11C]cyanation and alkaline hydrolysis reactions were performed consecutively in a single pot without a time-consuming intermediate purification step. The entire production time for this updated procedure is 55 min, which dramatically simplifies the entire synthesis and reduces the starting radioactivity required for a whole plant imaging study.

KW - Carbon-11 labeled indole-3-acetic acid

KW - Nucleophilic [C]cyanation

KW - Tetraethylene glycol

KW - Two-step one-pot

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DO - 10.1016/j.tetlet.2014.12.014

M3 - Article

AN - SCOPUS:84920183632

SN - 0040-4039

VL - 56

SP - 517

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 3

ER -

Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-¹¹C]acetic acid

Abstract

Keywords

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