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A direct, efficient method for the preparation of n6-protected 15n-labeled adenosines

Montserrat Terrazas1, Xavier Ariza, Jaume Farràs

  • 1Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, 08028 Barcelona, Spain.

The Journal of Organic Chemistry
|August 4, 2004
PubMed

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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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...