An exceptionally mild deprotection of phthalimides
John O. Osby, Michael G. Martin and Bruce Ganem*
*Department of Chemistry, Baker Laboratory Cornell University, Ithaca, New
York 14853 USA, Email: bg18
cornell.edu
J. O. Osby, M. G. Martin, B. Ganem, Tetrahedron Lett., 1984, 25, 2093-2096.
DOI: 10.1016/S0040-4039(01)81169-2
Abstract
Phthalimides are converted to primary amines in an efficient, two-stage, one-flask operation using NaBH4/2-propanol, then acetic acid. Phthalimides of α-amino acids are smoothly deprotected with no measurable loss of optical activity.
see article for more examples
reaction pathway
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Key Words
Phthalimides, Sodium Borohydride
ID: J72-Y1984-090
