Synthesis of methyl 2-(fluoromethyl)-3-fluoroalanine

Article abstract of DOI:10.1055/s-1994-25552

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 of their solutions.