An improved synthesis of PET dopamine D2 receptors radioligand [11c]raclopride

Xiangshu Fei; Bruce H. Mock; Timothy R. DeGrado; Ji Quari Wang; Barbara E. Glick-Wilson; Michael L. Sullivan; Gary D. Hutchins; Qi Huang Zheng

doi:10.1081/SCC-120034174

An improved synthesis of PET dopamine D₂ receptors radioligand [¹¹c]raclopride

Xiangshu Fei, Bruce H. Mock, Timothy R. DeGrado, Ji Quari Wang, Barbara E. Glick-Wilson, Michael L. Sullivan, Gary D. Hutchins, Qi Huang Zheng

Radiology

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

34 Scopus citations

Abstract

An improved synthesis of [¹¹C]raclopride is reported. The precursor desmethyl-raclopride was synthesized from 3,5-dichloro-2,6-dimethoxybenzoic acid and (S)-(-)-2-aminoethyl-1-ethylpyrrolidine via a straight-forward, four-step synthetic approach with 29% overall chemical yield. [¹¹C]Raclopride was prepared by O-[¹¹C]methylation of the precursor with [ ¹¹C]methyl triflate and purification with a semi-preparative HPLC method in 20-34% radiochemical yield, based on [¹¹C]methyl bromide, decay corrected to end of bombardment (EOB).

Original language	English (US)
Pages (from-to)	1897-1907
Number of pages	11
Journal	Synthetic Communications
Volume	34
Issue number	10
DOIs	https://doi.org/10.1081/SCC-120034174
State	Published - 2004

Keywords

Dopamine D receptors
Positron emission tomography
Radioligand
Synthesis
[C]Raclopride

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1081/SCC-120034174

Cite this

@article{51682fc6c1df4f228957b3e436c87457,

title = "An improved synthesis of PET dopamine D2 receptors radioligand [11c]raclopride",

abstract = "An improved synthesis of [11C]raclopride is reported. The precursor desmethyl-raclopride was synthesized from 3,5-dichloro-2,6-dimethoxybenzoic acid and (S)-(-)-2-aminoethyl-1-ethylpyrrolidine via a straight-forward, four-step synthetic approach with 29% overall chemical yield. [11C]Raclopride was prepared by O-[11C]methylation of the precursor with [ 11C]methyl triflate and purification with a semi-preparative HPLC method in 20-34% radiochemical yield, based on [11C]methyl bromide, decay corrected to end of bombardment (EOB).",

keywords = "Dopamine D receptors, Positron emission tomography, Radioligand, Synthesis, [C]Raclopride",

author = "Xiangshu Fei and Mock, {Bruce H.} and DeGrado, {Timothy R.} and Wang, {Ji Quari} and Glick-Wilson, {Barbara E.} and Sullivan, {Michael L.} and Hutchins, {Gary D.} and Zheng, {Qi Huang}",

note = "Funding Information: This work was partially supported by the Indiana 21st Century Research and Technology Fund, and the Lilly Endowment Inc. to the Indiana Genomics Initiative (INGEN) of Indiana University.",

year = "2004",

doi = "10.1081/SCC-120034174",

language = "English (US)",

volume = "34",

pages = "1897--1907",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis Ltd.",

number = "10",

}

TY - JOUR

T1 - An improved synthesis of PET dopamine D2 receptors radioligand [11c]raclopride

AU - Fei, Xiangshu

AU - Mock, Bruce H.

AU - DeGrado, Timothy R.

AU - Wang, Ji Quari

AU - Glick-Wilson, Barbara E.

AU - Sullivan, Michael L.

AU - Hutchins, Gary D.

AU - Zheng, Qi Huang

N1 - Funding Information: This work was partially supported by the Indiana 21st Century Research and Technology Fund, and the Lilly Endowment Inc. to the Indiana Genomics Initiative (INGEN) of Indiana University.

PY - 2004

Y1 - 2004

N2 - An improved synthesis of [11C]raclopride is reported. The precursor desmethyl-raclopride was synthesized from 3,5-dichloro-2,6-dimethoxybenzoic acid and (S)-(-)-2-aminoethyl-1-ethylpyrrolidine via a straight-forward, four-step synthetic approach with 29% overall chemical yield. [11C]Raclopride was prepared by O-[11C]methylation of the precursor with [ 11C]methyl triflate and purification with a semi-preparative HPLC method in 20-34% radiochemical yield, based on [11C]methyl bromide, decay corrected to end of bombardment (EOB).

AB - An improved synthesis of [11C]raclopride is reported. The precursor desmethyl-raclopride was synthesized from 3,5-dichloro-2,6-dimethoxybenzoic acid and (S)-(-)-2-aminoethyl-1-ethylpyrrolidine via a straight-forward, four-step synthetic approach with 29% overall chemical yield. [11C]Raclopride was prepared by O-[11C]methylation of the precursor with [ 11C]methyl triflate and purification with a semi-preparative HPLC method in 20-34% radiochemical yield, based on [11C]methyl bromide, decay corrected to end of bombardment (EOB).

KW - Dopamine D receptors

KW - Positron emission tomography

KW - Radioligand

KW - Synthesis

KW - [C]Raclopride

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U2 - 10.1081/SCC-120034174

DO - 10.1081/SCC-120034174

M3 - Article

AN - SCOPUS:2942529084

SN - 0039-7911

VL - 34

SP - 1897

EP - 1907

JO - Synthetic Communications

JF - Synthetic Communications

IS - 10

ER -