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Neurotrophic peptide aldehydes: solid phase synthesis of fellutamide B and a simplified analog

John S Schneekloth1, John L Sanders, John Hines

  • 1Department of Molecular, Cellular, and Developmental Biology, Yale University, PO Box 208103, New Haven, CT 06520-8103, USA.

Bioorganic & Medicinal Chemistry Letters
|May 16, 2006
PubMed

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Preparation of 1° Amines: Gabriel Synthesis01:28

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...