161011-01-4Relevant academic research and scientific papers
Synthesis of N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl} amine
Fleck, Thomas J.,McWhorter Jr., William W.,DeKam, Richard N.,Pearlman, Bruce A.
, p. 9612 - 9617 (2003)
N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl} amine (1)1 is a key intermediate in the preparation of premafloxacin (2), which was under development as an antibiotic for use against pathogens of veterinary importance. This paper describes the development of a practical, efficient, and stereoselective process for the preparation of 1 from isobutyl (3S)-3-{methyl[(1S)-1-phenylethyl]-amino}butanoate (5c). The key steps in the synthetic sequence are an asymmetric Michael addition, which yields 5c, and a stereoselective alkylation, which yields (3S,4S)-3-allyl-1,4-dimethylazetidin-2-one (17).
