Simplified Synthesis of Isotopically Labeled 5,5-Dimethyl-pyrroline N-Oxide

Abstract

5,5-Dimethylpyrroline N-oxide (15N) and 5,5-di(trideuteromethyl)pyrroline N-oxide were synthesized from the respective isotopically labeled 2-nitropropane analogs obtained from the reaction of sodium nitrate with 2-halopropanes. This facile, straightforward process allows synthesizing isotopically labeled DMPO analogs in a 4-step reaction without special equipment.

Synthesis and evaluation of 13C-labeled 5-5-dimethyl-1-pyrroline-N-oxide aimed at in vivo detection of reactive oxygen species using hyperpolarized 13C-MRI

“…Since the initial synthesis of unlabeled DMPO (34,35) several other researchers have synthesized DMPO and its analogs using various routes (36)(37)(38)(39)(40)(41)(42). Based on works of Beth et al (43) and Janzen et al (38), synthesis of labeled DMPO as a spin trap agent was first explored by Pou et al (37).…”

“…Based on works of Beth et al (43) and Janzen et al (38), synthesis of labeled DMPO as a spin trap agent was first explored by Pou et al (37). In order to prepare DMPO with 13 C at position C5 and deuterated protons on neighboring carbons (to prolong the T1 relaxation times) we followed the procedure of Le et al (41) and Leinisch et al (42). We found that the 13 C-C2 deuterated three carbon starting material could be effectively prepared from, the h-d exchange on acetone 13 C-C2 as described in the literature (44) under basic conditions.…”