Synthesis of carbon‐14 labeled vigabatrin

Abstract

Carbon‐14 labeled vigabatrin was synthesized in 5 steps from 5‐hydroxymethyl‐2‐pyrrolidone tosylate and NaCN‐[14C]. A key step involved reduction of the resulting nitrile in the presence of excess dimethylamine to give the dimethylamino‐ethyl 2‐pyrrolidone derivative in one step. This afforded an overall radiochemical yield of 22% and radiochemical purity greater than 98%.

Synthesis of γ‐Aminobutyric Acid Analogs

“…After displacement of the tosylate by cyanide, reduction of the resulting nitrile (155) (2) with an overall radiochemical yield of 22% and radiochemical purity greater than 98% [127]. (S)-Vigabatrin (S)- (2) has been prepared in 38% overall yield and 90% enantiomeric purity via a Wittig reaction of the w-aldehyde of glutamic acid and methyl triphenylphosphonium bromide [128].…”

Novel synthesis of [1‐11C]γ‐vinyl‐γ‐aminobutyric acid ([1–11C]GVG) for pharmacokinetic studies of addiction treatment

“…[11][12][13][14][15] For example, a procedure to prepare the key 2-oxopyrrolidine-5-carboxaldehyde precursor that would in principle allow the incorporation of C-11 by employing the Wittig condensation with [ 11 C]methyltriphenylphosphonium iodide (Scheme 1) was not straightforward. [14][15][16] We experienced this in our initial trials, and other researchers (authors in References 14,15 ) made similar observations.…”