Diprotection of primary amines as N-substituted-2,5-bis[(triisopropylsilyl)oxy]pyrroles (BIPSOP)

✍ Scribed by Stephen F. Martin; Chris Limberakis

• Book ID: 104256810
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 195 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00443-7

✦ Synopsis

Primary amines are diprotected as their 2,5-bis[(triisopropylsilyl)oxy]pyrrole derivatives (BIPSOP). This protecting group is stable to strong bases such as organolithiums and alkoxides at 0 °C and to temperatures up to about 150 °C. Removal may be accomplished by a mild two step sequence.