1-Phenethylamine, (-)- → (2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid

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Reaction Steps

(R/S)-2-Hydroxy-2-methyl-3,3,3-trifluoropropanoic acid was resolved according to the resolution method described in European Patent Application No. EP 524781 (described for the preparation of the (S)-(−)-acid) except that (1S,2R)-norephedrine was used in place of (1R,2S)-norephedrine or (S)-(−)-1-phenylethylamine to yield the title compound, [α]D20 +18.1° C. (c, 8.8 in MeOH); NMR analysis of the acid in the presence of (R)-(+)-1-phenylethylaine gave an enantiomerical purity of >98%. NMR (CDCl3): 1.27 (s, 3H) for the (R)-enantiomer, 1.21 (s, 3H) for the (S)-enantiomer.

Provenance & Evidence