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Synthesis of 11C-labelled Alkyl Iodides: Using Non-thermal Plasma and Palladium-mediated Carbonylation Methods
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.ORCID iD: 0000-0003-0241-092X
2006 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Compounds labelled with 11C (β+, t1/2 = 20.4 min) are used in positron emission tomography (PET), which is a quantitative non-invasive molecular imaging technique. It utilizes computerized reconstruction methods to produce time-resolved images of the radioactivity distribution in living subjects.

The feasibility of preparing [11C]methyl iodide from [11C]methane and iodine via a single pass through a non-thermal plasma reactor was explored. [11C]Methyl iodide with a specific radioactivity of 412 ± 32 GBq/µmol was obtained in 13 ± 3% decay-corrected radiochemical yield within 6 min via catalytic hydrogenation of [11C]carbon dioxide (24 GBq) and subsequent iodination, induced by electron impact.

Labelled ethyl-, propyl- and butyl iodide was synthesized, within 15 min, via palladium-mediated carbonylation using [11C]carbon monoxide. The carbonylation products, labelled carboxylic acids, esters and aldehydes, were reduced to their corresponding alcohols and converted to alkyl iodides. [1-11C]Ethyl iodide was obtained via palladium-mediated carbonylation of methyl iodide with a decay-corrected radiochemical yield of 55 ± 5%. [1-11C]Propyl iodide and [1-11C]butyl iodide were synthesized via the hydroformylation of ethene and propene with decay-corrected radiochemical yields of 58 ± 4% and 34 ± 2%, respectively. [1-11C]Ethyl iodide was obtained with a specific radioactivity of 84 GBq/mmol from 10 GBq of [11C]carbon monoxide. [1-11C]Propyl iodide was synthesized with a specific radioactivity of 270 GBq/mmol from 12 GBq and [1-11C]butyl iodide with 146 GBq/mmol from 8 GBq.

Palladium-mediated hydroxycarbonylation of acetylene was used in the synthesis of [1-11C]acrylic acid. The labelled carboxylic acid was converted to its acid chloride and subsequently treated with amine to yield N-[carbonyl-11C]benzylacrylamide. In an alternative method, [carbonyl-11C]acrylamides were synthesized in decay-corrected radiochemical yields up to 81% via palladium-mediated carbonylative cross-coupling of vinyl halides and amines. Starting from 10 ± 0.5 GBq of [11C]carbon monoxide, N-[carbonyl-11C]benzylacrylamide was obtained in 4 min with a specific radioactivity of 330 ± 4 GBq/µmol.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis , 2006. , p. 47
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 227
Keywords [en]
Organic chemistry, isotopic labelling, carbon-11, alkyl iodides, acrylamides, specific radioactivity, carbonylation, carbon monoxide, non-thermal plasma, PET
Keywords [sv]
Organisk kemi
National Category
Natural Sciences
Identifiers
URN: urn:nbn:se:uu:diva-7171ISBN: 91-554-6671-0 (print)OAI: oai:DiVA.org:uu-7171DiVA, id: diva2:168959
Public defence
2006-10-27, B42, BMC, Husaregatan 3, Uppsala, 13:15
Opponent
Supervisors
Available from: 2006-10-05 Created: 2006-10-05 Last updated: 2013-10-02Bibliographically approved
List of papers
1. [C-11]methyl iodide from [C-11]methane and iodine using a non-thermal plasma method
Open this publication in new window or tab >>[C-11]methyl iodide from [C-11]methane and iodine using a non-thermal plasma method
2006 (English)In: Journal of labelled compounds & radiopharmaceuticals, ISSN 0362-4803, E-ISSN 1099-1344, Vol. 49, no 13, p. 1177-1186Article in journal (Refereed) Published
Abstract [en]

A method and an apparatus for preparing [C-11]methyl iodide from [C-11]methane and iodine in a single pass through a non-thermal plasma reactor has been developed. The plasma was created by applying high voltage (400 V/31 kHz) to electrodes in a stream of helium gas at reduced pressure. The [C-11]methane used in the experiments was produced from [C-11]carbon dioxide via reduction with hydrogen over nickel. [C-11]methyl iodide was obtained with a specific radioactivity of 412 +/- 32 GBq/mu mol within 6 min from approximately 24 GBq of [C-11]carbon dioxide. The decay corrected radiochemical yield was 13 +/- 3% based on [C-11]carbon dioxide at start of synthesis. [C-11]Flumazenil was synthesized via a N-alkylation with the prepared [C-11]methyl iodide.

Keywords
[C-11]methyl iodide, [C-11]methane, non-thermal plasma, specific radioactivity
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-94929 (URN)10.1002/jlcr.1135 (DOI)000242796700006 ()
Available from: 2006-10-05 Created: 2006-10-05 Last updated: 2017-12-14Bibliographically approved
2. Synthesis of [1-11C]ethyl iodide from carbon monoxide and its application in alkylation reactions
Open this publication in new window or tab >>Synthesis of [1-11C]ethyl iodide from carbon monoxide and its application in alkylation reactions
2004 (English)In: Journal of Labelled Compounds and Radiopharmaceuticals, ISSN 0362-4803, Vol. 47, no 11, p. 723-731Article in journal (Refereed) Published
National Category
Natural Sciences
Identifiers
urn:nbn:se:uu:diva-94930 (URN)
Available from: 2006-10-05 Created: 2006-10-05 Last updated: 2015-09-24
3. Synthesis of [1-C-11]propyl and [1-C-11]butyl iodide from [C-11]carbon monoxide and their use in alkylation reactions
Open this publication in new window or tab >>Synthesis of [1-C-11]propyl and [1-C-11]butyl iodide from [C-11]carbon monoxide and their use in alkylation reactions
2006 (English)In: Journal of labelled compounds & radiopharmaceuticals, ISSN 0362-4803, E-ISSN 1099-1344, Vol. 49, no 12, p. 1105-1116Article in journal (Refereed) Published
Abstract [en]

A method to prepare [1-C-11]propyl iodide and [1-C-11]butyl iodide from [C-11]carbon monoxide via a three step reaction sequence is presented. Palladium mediated formylation of ethene with [C-11]carbon monoxide and hydrogen gave [1-C-11]propionaldehyde and [1-C-11]propionic acid. The carbonylation products were reduced and subsequently converted to [1-C-11]propyl iodide. Labelled propyl iodide was obtained in 58 +/- 4% decay corrected radiochemical yield and with a specific radioactivity of 270 +/- 33 GBq/mu mol within 15 min from approximately 12 GBq of [C-11]carbon monoxide. The position of the label was confirmed by C-13-labelling and C-13-NMR analysis. [1-C-11]Butyl iodide was obtained correspondingly from propene and approximately 8 GBq of [C-11]carbon monoxide, in 34 +/- 2% decay corrected radiochemical yield and with a specific radioactivity of 146 +/- 20 GBq/mu mol. The alkyl iodides were used in model reactions to synthesize [O-propyl-1-C-11]propyl and [O-butyl-1-C-11]butyl benzoate. Propyl and butyl analogues of etomidate, a (beta-11-hydroxylase inhibitor, were also synthesized.

Keywords
[C-11]carbon monoxide, [1-C-11]propyl iodide, [1-C-11]butyl iodide, carbonylation, formylation, alkylation
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-94931 (URN)10.1002/jlcr.1119 (DOI)000242335900009 ()
Available from: 2006-10-05 Created: 2006-10-05 Last updated: 2017-12-14Bibliographically approved
4. Synthesis of [11C]/[13C]acrylamides by palladium-mediated carbonylation
Open this publication in new window or tab >>Synthesis of [11C]/[13C]acrylamides by palladium-mediated carbonylation
2007 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 3, p. 455-461Article in journal (Refereed) Published
Abstract [en]

Two methods are presented for the synthesis of acrylamides labelled with C-11 (beta(+), t(1/2) = 20.4 min) and C-11 in the carbonyl position. In the first method, [1-C-11]acrylic acid is synthesised from [C-11]carbon monoxide by palladium-mediated hydroxy-carbonylation of acetylene. The labelled carboxylic acid is converted into the acyl chloride and subsequently treated with amine to yield N-benzyl[carbonyl(11)C]acrylamide, The second method utilizes [C-11]carbon monoxide in a palladium-mediated carbonylative cross-coupling of vinyl halides and amines. A higher radiochemical yield is achieved with the latter method and the amount of amine needed is decreased to 1/20. The C-11-labelled acrylamides were isolated in up to 81 % decay-corrected radiochemical yield. Starting from 10 +/- 0.5GBq of [C-11]carbon monoxide, N-benzyl[carbonyl-C-11]acrylamide was obtained in 4 min with a specific radioactivity of 330 +/- 4 GBq mu mol-(1). Co-labelling with C-11 and C-13 enabled confirmation of the labelled position by C-13 NMR spectroscopy.

Keywords
Carbonylation, Amides, Carbon monoxide, Isotopic labelling, Carbon-11, 11C, PET
National Category
Chemical Sciences
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-98592 (URN)10.1002/ejoc.200600700 (DOI)000243600100007 ()
Available from: 2009-02-27 Created: 2009-02-27 Last updated: 2017-12-13Bibliographically approved
5. [1-11C]Ethyl iodide and [1-11C]propyl iodide in the synthesis of two potential NK1-receptor ligands and initial PET-imaging
Open this publication in new window or tab >>[1-11C]Ethyl iodide and [1-11C]propyl iodide in the synthesis of two potential NK1-receptor ligands and initial PET-imaging
Show others...
(English)Manuscript (Other academic)
National Category
Medicinal Chemistry
Identifiers
urn:nbn:se:uu:diva-94933 (URN)
Available from: 2006-10-05 Created: 2006-10-05 Last updated: 2018-01-13

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