Synthesis of diethyl [carbonyl-11C]malonate from [11C]carbon monoxide by rhodium-promoted carbonylation and its application as a reaction intermediate

Barletta, Julien; Karimi, Farhad; Doi, Hisashi; Långström, Bengt

doi:10.1002/jlcr.1098

Cited by 23 publications

(24 citation statements)

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“…This method provides a new way of synthesizing [ 11 C]hydroxyurea with more accurate chemical yield and greater radiochemical purity compared to earlier methods [202]. This general methodology for the synthesis of carbon-11 labeled urea and its derivatives was also explored in the radiosynthesis of diethyl [carbonyl-11 C]malonate, which was prepared in 50% radiochemical yield [203].…”

Section: Rhodium-mediated Carbonylationmentioning

confidence: 98%

C-11 Radiochemistry in Cancer Imaging Applications

Mach

2010

CTMC

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Carbon-11 (C-11) radiotracers are widely used for the early diagnosis of cancer, monitoring therapeutic response to cancer treatment, and pharmacokinetic investigations of anticancer drugs. PET imaging permits non-invasive monitoring of metabolic processes and molecular targets, while carbon-11 radiotracers allow a "hot-for cold" substitution of biologically active molecules. Advances in organic synthetic chemistry and radiochemistry as well as improved automated techniques for radiosynthesis have encouraged investigators in developing carbon-11 tracers for use in oncology imaging studies. The short half-life of carbon-11 (20.38 minutes) creates special challenges for the synthesis of C-11 labeled tracers; these include the challenges of synthesizing C-11 target compounds with high radiochemical yield, high radiochemical purity and high specific activity in a short time and on a very small scale. The optimization of conditions for making a carbon-11 tracer include the late introduction of the C-11 isotope, the rapid formation and purification of the target compound, and the use of automated systems to afford a high yield of the target compound in a short time. In this review paper, we first briefly introduce some basic principles of PET imaging of cancer; we then discuss principles of carbon-11 radiochemistry, focus on specific advances in radiochemistry, and describe the synthesis of C-11 radiopharmaceuticals developed for cancer imaging. The carbon-11 radiochemistry approaches described include the N,O, and S-alkylations of [(11)C]methyl iodide/[(11)C]methyl triflate and analogues of [(11)C]methyl iodide and their applications for making carbon-11 tracers; we then address recent advances in exploring a transmetallic complex mediated [(11)C]carbonyl reaction for oncologic targets.

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Section: Rhodium-mediated Carbonylationmentioning

confidence: 98%

C-11 Radiochemistry in Cancer Imaging Applications

Mach

2010

CTMC

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“…[110] Abgelöst wurde dieses Verfahren durch die Einführung von Hochdruckreaktionssystemen (HPLC-Mikroautoklaven) [36,37] [117] oder 1,2,2,6,6-Pentamethylpiperidin [118] Rhodiumvermittelte Carbonylierungen [122][123][124] sind eine weitere Möglichkeit zur Einführung von [ 11 C]CO in organische Moleküle.…”

Section: Bei Den Stille-kreuzkupplungen Mit [unclassified

“…11 C-markierte Malonate, [123] Hydroxyharnstoffe, [122] Carbamate [124] und Diphenylharnstoffe [124] …”

Section: Bei Den Stille-kreuzkupplungen Mit [unclassified

“…[189] Die Nitrilgruppe kann anschließend in reaktive Gruppen wie N-(4-[ 18 F]Fluorbenzyl)-2-bromacetamid umgewandelt werden, das zur 18 F-Markierung von Peptiden und Oligonucleotiden dient (siehe Abschnitt 3.5.1). [190] Die vielfältigen Anwendungen palladiumkatalysierter Kreuzkupplungen in der organischen Chemie (Heck-, Stille-, Suzuki-Miyaura-, Negishi-, Sonogashira-und BuchwaldHartwig-Reaktionen) [123,124,[191][192][193][194] haben auch in der Radiochemie ihren Niederschlag gefunden. Eine potenziell wichtige Anwendung der palladiumkatalysierten Kreuzkupplung, [195,196] in nucleophilen 18 F-Substitutionen hat sich als extrem nützliche Alternative zur Synthese einer Reihe einfacher 18 F-Fluorarene erwiesen, die durch andere konventionelle Verfahren nicht zugänglich sind.…”

Section: Bei Den Stille-kreuzkupplungen Mit [unclassified

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Synthese von ¹¹C‐, ¹⁸F‐, ¹⁵O‐ und ¹³N‐Radiotracern für die Positronenemissionstomographie

et al. 2008

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Die Positronenemissionstomographie (PET) ist eine leistungsfähige Bildgebungsmethode, die zur Untersuchung und Visualisierung der menschlichen Physiologie eingesetzt wird. Das Funktionsprinzip der PET beruht auf der Detektion positronenemittierender Radiopharmazeutika. Aus PET‐Experimenten können direkte Informationen über Stoffwechselvorgänge, Rezeptor‐Enzym‐Funktionen und biochemische Mechanismen im lebenden Gewebe erhalten werden. Anders als die Magnetresonanztomographie (MRT) und die Computertomographie (CT), die in erster Linie anatomische Bilder liefern, kann die PET chemische Veränderungen messen, die bereits vor dem Auftreten anatomischer Krankheitszeichen auftreten. Die PET ist dabei, sich als eine revolutionäre Methode für die Diagnostik von Körperfunktionen zu etablieren, die die Anwendung individueller, auf den Patienten zugeschnittener Behandlungsmethoden ermöglicht. Allerdings ist die Entwicklung von Synthesestrategien für neuartige positronenemittierende Moleküle nicht trivial. In diesem Aufsatz diskutieren wir die entscheidenden Aspekte bei der Synthese von PET‐Radiotracern mit den kurzlebigen Positronenemittern 11C, 18F, 15O und 13N. Der Schwerpunkt liegt auf den jüngsten Fortschritten bei der Entwicklung von Radiomarkierungsstrategien. Wir hoffen, dass dieser Aufsatz das Interesse von Synthesechemikern auch außerhalb der Radiochemie finden wird und die Bedeutung der PET in der molekularen Bildgebung sowie den Bedarf an neuen, innovativen chemischen Strategien für verbesserte Radiomarkierungstechniken aufzeigt.

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“…has explored the possibility of synthesizing diethyl [carbonyl-11 C]malonate from ethyl diazoacetate via a rhodium-mediated carbonylation reaction [238]. This compound was further used in subsequent alkylation step using ethyl iodide and tetrabutylammonium fluoride to obtain diethyl [carbonyl-11 C]malonate in 50% analytical radiochemical yield.…”

Section: B Selenium-mediated Carbonylationmentioning

confidence: 99%

State of Art in 11C Labelled Radiotracers Synthesis

Allard

Fouquet

James

et al. 2008

CMC

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Positron Emission Tomography has become a powerful scientific and clinical tool probing biochemical processes in the human body. Their clinical applications have proven to be vital in the evaluation and diagnosis of diseases. This is due, in large part, to advances in instrumentation and synthetic chemistry. Carbon-11 is a valuable radionuclide in PET as it virtually permits the synthesis of radiolabelled versions of any compound of interest. The syntheses with carbon-11 present several features: limited number of labelled precursors, sub-micromolar amounts of the starting materials, and a need for the introduction of the radioisotope as late as possible in the synthesis. All of these reasons have restricted complex radiosyntheses. The short half-life of carbon-11 (20.4 min) requires the rapid preparation and purification of carbon-11 labelled molecules. Those have to be carried out immediately before use from cyclotron produced precursors ([11C]CO2, [11C]CO, [11C]CH4) or reagents rapidly prepared from them ([11C]CH3I, [11C]COCl2, [11C]HCN). As a consequence carbon-11 has been underused compared to fluorine-18. However, because of the increasing molecular complexity and diversity of biologically active compounds, there is a need for new methodologies giving access in short time and high yield to radioactive (11)C-probes. The aim of this review is to emphasize the methodologies used in this field and to give a comprehensive overview of the numerous advances, which occurred over the past decade. In addition, for each labelling technique or reaction reported, a special attention has been brought to classify the applications in function of the targeted medical domain.

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Synthesis of diethyl [carbonyl-11C]malonate from [11C]carbon monoxide by rhodium-promoted carbonylation and its application as a reaction intermediate

Cited by 23 publications

References 23 publications

C-11 Radiochemistry in Cancer Imaging Applications

C-11 Radiochemistry in Cancer Imaging Applications

Synthese von ¹¹C‐, ¹⁸F‐, ¹⁵O‐ und ¹³N‐Radiotracern für die Positronenemissionstomographie

State of Art in 11C Labelled Radiotracers Synthesis

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Synthesis of diethyl [carbonyl-11C]malonate from [11C]carbon monoxide by rhodium-promoted carbonylation and its application as a reaction intermediate

Cited by 23 publications

References 23 publications

C-11 Radiochemistry in Cancer Imaging Applications

C-11 Radiochemistry in Cancer Imaging Applications

Synthese von 11C‐, 18F‐, 15O‐ und 13N‐Radiotracern für die Positronenemissionstomographie

State of Art in 11C Labelled Radiotracers Synthesis

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Product

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Synthese von ¹¹C‐, ¹⁸F‐, ¹⁵O‐ und ¹³N‐Radiotracern für die Positronenemissionstomographie