Molecules containing pyrrolidine core structures have attracted considerable interest due to their therapeutic applications and potential as well as their catalytic applications. Consequently, a number of methods for their asymmetric synthesis have been developed. However, there are few reports that detail the chiral separation of mixtures of pyrrolidine enantiomers. Herein we describe the enantiomeric separation of N-tosylated and N-benzhydrylated pyrrolidine alcohols and their precursor �-amino alcohols. These separations were achieved on polysaccharide-based HPLC chiral stationary phases (Chiralpak IA) using either normal or polar organic mobile phases. A better separation factor and resolution were obtained for N-tosylated pyrrolidine alcohol compared with the benzhydryl pyrrolidine alcohol. The chiral helical groove provided potential interaction sites for the recognition of the targeted compounds principally through pi-pi interactions and hydrogen bonding. The results also indicated the potential for scale-up from analytical to preparative separation of the targeted compounds.

HPLC separation of enantiomeric pyrrolidine alcohols and their precursors on polysaccharide-based chiral stationary phases

248th National Meeting (2014)

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