Synthesis of α-acetoxy-N-nitroso-4[3H]-pyrrolidine

Article abstract of DOI:10.1002/jlcr.2580160307

Tritium labeled α-acetoxy-N-nitroso-4[³H]-pyrrolidine 3, an important model compound used in the study of the metabolism of nitrosopyrrolidine, has been prepared from commercially available 4[³H]-l-proline. The synthesis involves two steps; first the nitrosation of the aminoacid to N-nitroso-4[³H]-l-proline 2, followed by the oxidative decarboxylation with lead tetraacetate in dichloromethane with 1.2 equivalents of pyridine to α-acetoxy-N-nitroso-4[³H]-pyrrolidine in 23% overall yield. The compound was further purified by HPLC.