Synthesis and Application of a New Fluorous-Tagged Ammonia Equivalent

✍ Scribed by Simon D. Nielsen; Garrick Smith; Mikael Begtrup; Jesper L. Kristensen

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 344 KB
• Volume: 16
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200903178

✦ Synopsis

Abstract

A novel fluorous‐tagged ammonia equivalent has been developed. It is based on a nitrogen–oxygen bond, which can be cleaved in a traceless manner by a molybdenum complex or samarium diiodide. The application in the synthesis of ureas, amides, sulfonamides, and carbamates is described. The scope of the fluorous NO linker is exemplified by the synthesis of itopride, a drug used for the treatment of functional dyspepsia. Itopride was synthesized with the aid of fluorous purification methods and the product was isolated in good overall yield, with high purity.