(S)-3-(Methylamino)-3-((R)-pyrrolidin-3-yl)propanenitrile is a key intermediate in the preparation of PF-00951966, a fluoroquinolone antibiotic for use against key pathogens causing community-acquired respiratory tract infections including multidrug resistant (MDR) organisms. This antibiotic when compared to the existing synthetic route, we are more efficient than existing synthetic route was developed to synthesize. (Z)-methyl 3 - ((R) -1 - ((S)-1-phenylethyl) aziridin-2-yl) acrylate as a starting material, Two key transformations in the synthetic sequence involve (a) stereoselctive nitro methane alkylation, (b) methylative aziridine ring-opening reaction with cyanide nucleophile.

Formal synthesis of PF-00951966: (S)-3-(methylamino)-3-((R)-pyrrolidin-3-yl)propanenitrile

248th National Meeting (2014)

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