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Nitroaldol reaction of nitro[ 11 C]methane to form 2‐(hydroxymethyl)‐2‐nitro[2‐ 11 C]propane‐1,3‐diol and [ 11 C]Tris
Author(s) -
Kato Koichi,
Zhang MingRong,
Minegishi Katsuyuki,
Nengaki Nobuki,
Takei Makoto,
Suzuki Kazutoshi
Publication year - 2011
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1833
Subject(s) - chemistry , hydroxymethyl , propane , nitro , nitroaldol reaction , tris , diol , nitro compound , formaldehyde , medicinal chemistry , methane , organic chemistry , catalysis , enantioselective synthesis , biochemistry , alkyl
The nitroaldol reaction of nitro[ 11 C]methane and formaldehyde, which yields 2‐(hydroxymethyl)‐2‐nitro[2‐ 11 C]propane‐1,3‐diol, is explored. The fluoride‐ion‐assisted nitroaldol reaction using (C 4 H 9 ) 4 NF was rapid and provided the desired nitrotriol in more than 97% radiochemical conversion (decay‐corrected) in 3 min at room temperature. Neither 2‐nitro[2‐ 11 C]ethanol nor 2‐nitro[2‐ 11 C]propane‐1,3‐diol was observed under the reaction conditions. The preparation of 2‐amino‐2‐(hydroxymethyl)‐[2‐ 11 C]propane‐1,3‐diol ([ 11 C]Tris) was described, which was followed by the nitro‐group reduction using NiCl 2 and NaBH 4 in aqueous MeOH. The decay‐corrected radiochemical conversion to [ 11 C]Tris was 68.0±6.5% in two steps. Copyright © 2010 John Wiley & Sons, Ltd.