Synthesis of [11C]/[13C]acrylamides by palladium-mediated carbonylation
Synthesis of [11C]/[13C]acrylamides by palladium-mediated carbonylation
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DOI：
10.1002/ejoc.200600700
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发表时间：
2007-01-01
影响因子：
2.8
通讯作者：
Langstrom, Bengt
中科院分区：
文献类型：
--
作者：
Eriksson, Jonas;Aberg, Ola;Langstrom, Bengt
本文介绍了两种合成C-11（β（+），t（1/2）= 20.4min）和C-11在羰基位置上标记的丙烯酰胺的方法。在第一种方法中，[1-C-11]丙烯酸由[C-11]一氧化碳通过钯介导的乙炔羟基羰基化合成。将标记的羧酸转化为酰氯，随后用胺处理以产生N-苄基[羰基（11）C]丙烯酰胺。第二种方法利用[C-11]一氧化碳在钯介导的卤代乙烯和胺的羰基化交叉偶联中。后一种方法获得了更高的放射化学产率，所需胺的量降低到1/20。C-11标记的丙烯酰胺以高达81%的衰变校正放射化学产率分离。从10 +/- 0.5GBq的[C-11]一氧化碳开始，在4分钟内得到比放射性为330 +/- 4 GBq μ mol-（1）的N-苄基[羰基-C-11]丙烯酰胺。用C-11和C-13共标记使得能够通过C-13 NMR光谱确认标记的位置。((c)Wiley-VCH Verlag GmbH & Co. KGaA，69451魏因海姆，德国，2007）。
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.((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).