Derivatization of chiral amines with (S,S)-N-trifluoroacetylproline anhydride for GC estimation of enantiomeric composition.

The reaction characteristics of (S,S)-N-trifluoroacetylproline anhydride were examined in an attempt to develop a quantitative GC assay of the enantiomers of the sterically hindered, chiral amine ketamine. With the aid of the individual enantiomers of ketamine and the corresponding synthetic N-trifluoroacetylprolyl amides, it was found that the derivatization reaction proceeds stereoselectively, in poor yield, and with some degree of racemization of the acylating reagent. The results indicate that care must be exercised when prolyl derivatizing reagents are chosen for assaying chiral amines.