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Synthesis of [11C]oxazolidinone via rhodium-mediated carbon-yaltion reaction using [11C]carbon monoxide and [11C]isocyanate intermediate
Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry.
Manuscript (Other academic)
URN: urn:nbn:se:uu:diva-94174OAI: oai:DiVA.org:uu-94174DiVA: diva2:167934
Available from: 2006-04-07 Created: 2006-04-07 Last updated: 2010-01-13Bibliographically approved
In thesis
1. [11C]Carbon Monoxide in Rhodium-/Palladium-Mediated Carbonylation Reactions
Open this publication in new window or tab >>[11C]Carbon Monoxide in Rhodium-/Palladium-Mediated Carbonylation Reactions
2006 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Methods for the 11C-labeling of carbonyl compounds applicable in the preparation of radiotracers for Positron Emission Tomography (PET) are described. To this end [11C]carbon monoxide at low concentration was used in transition metal- mediated reactions.

Stille couplings were employed in the synthesis of [carbonyl-11C]ketones from methyl and aryl halides with [11C]carbon monoxide. The synthesized [carbonyl-11C]ketones were obtained from the corresponding organostannanes with analytical radiochemical yields up to 98%.

A number of synthetic routes were designed using [11C]carbon monoxide and rhodium complexes. Nitrene intermediates were generated from azides and reacted via a rhodium-mediated carbonylation reaction as a general synthetic route to [carbonyl-11C]isocyanates, versatile precursors. [carbonyl-11C]Isocyanate reacted via nucleophilic attack of an amine to form N,N’-diphenyl[11C]urea in 82% analytical radiochemical yield, ethyl phenyl[11C]carbamate was synthesized by the same route, using ethanol as the nucleophile, in 70% radiochemical yield. [11C]Isocyanate was also able to react in a [2+3] cycloaddition with ethylene oxide to form 3-phenyl[carbonyl-11C]oxazolidin-2-one in over 80% analytical radiochemical yield. This method was applied to the synthesis of a potential efflux system tracer [11C]hydroxyurea in 38% isolated radiochemical yield and the derivative 1-hydroxy-3-phenyl[11C]urea in 35% isolated radiochemical yield. Carbene intermediates, generated from diazo compounds, were reacted with [11C]carbon monoxide in the rhodium-mediated synthesis of [carbonyl-11C]ketenes. [carbonyl-11C]Ketene intermediates were utilised in the synthesis of diethyl[carbonyl-11C]malonate, from ethyl diazoacetate and ethanol. The product was obtained with a 20% isolated radiochemical yield. Alkylation of diethyl[carbonyl-11C]malonate, with ethyliodide and tetrabutylammonium fluoride, was successfully accomplished and diethyl diethyl[carbonyl-11C]malonate was synthesized in 50% analytical radiochemical yield. Several (carbonyl-13C)compounds were also synthesized using the described methods as a way of characterizing the position of the label using 13C-NMR.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2006. 50 p.
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 156
Organic chemistry, carbonylation reaction, carbon monoxide, PET, 11C-labelling, rhodium, palladium, Organisk kemi
National Category
Organic Chemistry
urn:nbn:se:uu:diva-6654 (URN)91-554-6500-5 (ISBN)
Public defence
2006-04-28, Room B22, BMC, Husarsgatan 3, Uppsala, 09:00
Available from: 2006-04-07 Created: 2006-04-07Bibliographically approved

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