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

✍ Scribed by Jose E. Saavedra; Lanny I. Hecker; James G. Farrelly

• Book ID: 102372659
• Publisher: John Wiley and Sons
• Year: 1979
• Tongue: French
• Weight: 199 KB
• Volume: 16
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580160307

✦ Synopsis

T r i t i u m l a b e l e d a-acetoxy-N-nitros0-4[~H]-pyrrol i d i n e 3, an important model compound used i n t h e study o f t h e metabolism o f n i t r o s o p y r r o l i d i n e , has been prepared from commercially a v a i l a b l e 4[3H1-b-proline.

The synthesis i n v o l v e s two steps; f i r s t the n i t r o s a t i o n of the aminoacid t o N-nitros0-4[~HI-Cp r o l i n e 2, followed by the o x i d a t i v e decarboxylation w i t h l e a d t e t r a a c e t a t e i n dichloromethane w i t h 1.2 equivalents o f p y r id i n e t o a-acetoxy-N-nitroso-4[3H]-pyrrol i d i n e i n 23% o v e r a l l y i e l d . The compound was f u r t h e r p u r i f i e d by HPLC.