Constance G. Chidester

Synthesis of (R)-N-[4-[4-(dibutylamino)-1-hydroxybutyl]phenyl]methanesulfonamide, (E)-2-butenedioate (2:1) salt (artilide fumarate) and the enantiomers of N-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide, (E)-2-butenedioate (2:1) salt (ibutilide fumarate)

Abstract Syntheses of artilide fumarate, its (S) enantiomer and the (R) and (S) enantiomers of ibutilide fumarate were achieved by reduction of the prochiral ketones with (+) and (−)-B-chlorodiisopinocampheylborane. Several methods for analyzing the optical purity of these compounds are presented. The absolute configurations were established by a single crystal X-ray crystallographic analysis of (S)-N-[4-[4-(dibutylamino)-1-hydroxy-4-oxobutyl]phenyl]methanesulfonamide.