Nitroaldol reaction of nitro[ 11 C]methane to form 2‐(hydroxymethyl)‐2‐nitro[2‐ 11 C]propane‐1,3‐diol and [ 11 C]Tris

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.