Photoinitiated Carbonylation with [¹¹C]Carbon Monoxide Using Amines and Alkyl Iodides

Abstract

Photoinitiated radical carbonylation with [(11)C]carbon monoxide at low concentration was employed in syntheses of carbonyl-(11)C-labeled amides using alkyl iodides and amines as precursors. Eleven (11)C-amides were synthesized in up to 74% decay-corrected radiochemical yields with reaction times of 400 s and with up to 95% conversion of carbon monoxide. Starting with 26.3 GBq of [(11)C]carbon monoxide, 10.6 GBq of 1-cyclohexane [(11)C]carbonyl-4-phenyl-piperazine (15) was obtained within 35 min from the end of bombardment (33 microA) and with a specific radioactivity of 192 GBq/micromol at the same time point. The influence of solvents was investigated. The described procedure extends the range of accessible labeling methods. The method may also be useful for preparation of (13)C- and (14)C-substituted compounds.

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

“…Identities of synthesized 13 C-labelled compound were determined using NMR. NMR spectra were recorded on a Varian XL 400 NMR spectrometer (Varian Inc., Palo Halto, USA) operating at 400 MHz, and chloroform-d 3 was used as internal standard.…”

“…5 This experimental setup had been successfully used to explore the reactivity of [ 11 12 and also in radical-mediated reactions. 13 All these methods permit the synthesis of 11 C-labelled compounds in high specific radioactivity in a range between 100 and 1500 GBq/mmol. 14 The presented method deals with the properties of diazo compounds to complex with rhodium complex to form a metallacarbene complex.…”

“…The position of the labelling was confirmed by synthesizing the 13 C-labelled product using ( 13 C)carbon monoxide at higher concentration. The labelled carbonyl position was identified by the 13 C-NMR analysis at 166.7 ppm which corresponds to the carbonyl carbon of the isotopically unmodified authentic reference compound. The specific radioactivity of the isolated diethyl [carbonyl-…”

Water Solvent Method for Esterification and Amide Formation between Acid Chlorides and Alcohols Promoted by Combined Catalytic Amines: Synergy between N‐Methylimidazole and N,N,N′,N′‐Tetramethylethylenediamine (TMEDA)

“…The following esters and amides obtained in this paper are known compounds: 1-octyl 3-phenylpropanoate, [9] 9-decen-1-yl 3-phenylpropanoate, [10] 6-chlorohexyl 3-phenylpropanoate, [10] 2-hexyn-1-yl 3-phenylpropanoate, [10] ethyl 6-(3-phenylpropanoyloxy)hexanoate, [10] phenyl 3-phenylpropanoate, [11] 1-phenylethyl 3-phenylpropanoate, [12] methallyl 3-phenylpropanoate, [13] 1-octyl cyclohexanecarboxylate, [14] 1-octyl 3,3-dimethylbutanoate, [15] 1-octyl benzoate, [10] 3-octyl benzoate, [16] 1-octyl methacrylate, [17] 1-ethynyl-2-methyl-2-pentenyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (chlovaporthrin: a vaporthrin analogue), [18] 3-phenoxybenyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (permethrin), [19] N-carbobenzoxy-l-proline phenylmethyl ester, [20] N-methyl-N-phenyl-3-phenylpropanamide, [21] N-phenyl-3-phenylpropanamide, [22] N-(4-chlorophenyl)-3-phenylpropanamide, [23] N-(2-chlorophenyl)-3-phenylpropanamide, [23] N-[(S)-1-phenylethyl]-3-phenylpropanamide, [10] N-(3-phenylpropionoyl)piperidine, [10] N-methoxy-N-methyl 3-phenylpropanamide, [24] N-(2,2-dimethoxyethyl)-3-phenylpropanamide, [25] N-methyl-N-phenylbenzamide, [26] N-phenylbenzamide, [27] N-benzoylpiperidine, [10] N-methyl-Nphenylcyclohexanamide, [28] N-phenylcyclohexanamide, [29] Ncyclohexanecarbonylpiperidine, [10] N-methyl-N-phenyl-3,3-dimethylbutanamide, [30] N-phenyl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanamide. [31] Typical Procedure for Esterification (Table 2, entry 1).…”

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

“…Lang-und kurzkettige aliphatische Carbonsäuren, [125,126] Ester [126][127][128] und Amide [129] [133] Auch die direkte Synthese von [Carbonyl-11 C]Amiden ausgehend von […”