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Efficient DBU accelerated synthesis of 18F-labelled trifluoroacetamides

Antonio Bermejo Gómez1, Miguel A Cortés González2, Marvin Lübcke2

  • 1AstraZeneca Personalised Healthcare and Biomarkers, PET Centre at Karolinska Institutet, Karolinska Universitetssjukhuset Solna, R5:02, SE-171 76 Stockholm, Sweden. Magnus.Schou@astrazeneca.com and Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory, SE-106 91 Stockholm, Sweden and Stockholm Brain Institute, Karolinska Institutet, SE-171 77 Stockholm, Sweden.

Chemical Communications (Cambridge, England)
|November 16, 2016
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...
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