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:
-
- Brookhaven National Laboratory (BNL), Upton, NY (United States); Stony Brook Univ., Stony Brook, NY (United States)
- 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)
- 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
- 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. https://doi.org/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. https://doi.org/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 = {Fri Dec 12 00:00:00 EST 2014},
month = {Fri Dec 12 00:00:00 EST 2014}
}
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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
Acid and 1, 2‐Dichloroethane Co‐Promoted Substitution of the Amino Groups in Gramine and its Analogues with Trialkyl Phosphites
journal, December 2019
- Guo, Shengmei; Zhang, Zhebin; Xu, Jianxin
- ChemistrySelect, Vol. 4, Issue 48