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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 ([11]IAA or [11]auxin). By replacing an aprotic polar solvent with tetraethylene glycol, nucleophilic [11]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.

Authors:
 [1];  [2];  [2];  [2];  [2];  [2];  [2]
  1. Brookhaven National Laboratory (BNL), Upton, NY (United States); Stony Brook Univ., Stony Brook, NY (United States)
  2. Brookhaven National Laboratory (BNL), Upton, NY (United States)
Publication Date:
Research Org.:
Brookhaven National Lab. (BNL), Upton, NY (United States). Positron Emission Tomography (PET) Facility
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1167431
Alternate Identifier(s):
OSTI ID: 1433587
Report Number(s):
BNL-107233-2014-JA
Journal ID: ISSN 0040-4039; R&D Project: MO-085; KP1602010
Grant/Contract Number:  
DE-SC00112704; AC02-98CH10886
Resource Type:
Accepted Manuscript
Journal Name:
Tetrahedron Letters
Additional Journal Information:
Journal Volume: 56; Journal Issue: 3; Journal ID: ISSN 0040-4039
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY; Carbon-11 labeled indole-3-acetic acid; nucleophilic [11C]cyanation; tetraethylene glycol; two-step one-pot; positron emission tomography (PET) facility

Citation Formats

Lee, Sojeong, Qu, Wenchao, Alexoff, David L., Shea, Colleen, Kim, Dohyun, Schueller, Michael, and Fowler, Joanna S. Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-11C]acetic acid. United States: N. p., 2014. Web. doi:10.1016/j.tetlet.2014.12.014.
Lee, Sojeong, Qu, Wenchao, Alexoff, David L., Shea, Colleen, Kim, Dohyun, Schueller, Michael, & Fowler, Joanna S. Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-11C]acetic acid. United States. doi:10.1016/j.tetlet.2014.12.014.
Lee, Sojeong, Qu, Wenchao, Alexoff, David L., Shea, Colleen, Kim, Dohyun, Schueller, Michael, and Fowler, Joanna S. Fri . "Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-11C]acetic acid". United States. doi:10.1016/j.tetlet.2014.12.014. https://www.osti.gov/servlets/purl/1167431.
@article{osti_1167431,
title = {Tetraethylene glycol promoted two-step, one-pot rapid synthesis of indole-3-[1-11C]acetic acid},
author = {Lee, Sojeong and Qu, Wenchao and Alexoff, David L. and Shea, Colleen and Kim, Dohyun and Schueller, Michael and Fowler, Joanna S.},
abstractNote = {An operationally friendly, two-step, one-pot process has been developed for the rapid synthesis of carbon-11 labeled indole-3-acetic acid ([11]IAA or [11]auxin). By replacing an aprotic polar solvent with tetraethylene glycol, nucleophilic [11]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.},
doi = {10.1016/j.tetlet.2014.12.014},
journal = {Tetrahedron Letters},
number = 3,
volume = 56,
place = {United States},
year = {2014},
month = {12}
}

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Works referencing / citing this record:

Synthesis of l -[4- 11 C]Asparagine by Ring-Opening Nucleophilic 11 C-Cyanation Reaction of a Chiral Cyclic Sulfamidate Precursor
journal, April 2018

  • Xu, Youwen; Cankaya, Aylin Sibel; Hoque, Ruma
  • Chemistry - A European Journal, Vol. 24, Issue 26
  • DOI: 10.1002/chem.201801029

Synthesis of l -[4- 11 C]Asparagine by Ring-Opening Nucleophilic 11 C-Cyanation Reaction of a Chiral Cyclic Sulfamidate Precursor
journal, April 2018

  • Xu, Youwen; Cankaya, Aylin Sibel; Hoque, Ruma
  • Chemistry - A European Journal, Vol. 24, Issue 26
  • DOI: 10.1002/chem.201801029