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Synthesis 1994; 1994(7): 701-702
DOI: 10.1055/s-1994-25552
short paper
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Synthesis of Methyl 2-(Fluoromethyl)-3-Fluoroalanine

Franklin A. Davis* , G. Venkat Reddy, Michal Bental, Carl J. Deutsch
  • *Department of Chemistry, Drexel University, Philadelphia 19104, USA
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Publication Date:
17 September 2002 (online)

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The title compound 1b, an important intracellular pH indicator, is conveniently prepared in 44% overall yield from 1,3-difluoro-2-propanol (2). Key steps in this synthesis include oxidation of 2 to 1,3-difluoroacetone (3) in near quantitative yield using KMnO4/CuSO4 and the addition of trimethylsilyl cyanide to a phenyl glycinol protected imine. The efficiency of this process was enhanced further by use of crude reaction mixtures or their solutions.