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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:

J. O. Osby, M. G. Martin, B. Ganem, Tetrahedron Lett., 1984, 25, 2093-2096.

DOI: 10.1016/S0040-4039(01)81169-2


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.

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reaction pathway

Key Words

Phthalimides, Sodium Borohydride

ID: J72-Y1984-090