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Synthesis of N-methyl-N-[(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl]amine

Synthesis of N-methyl-N-[(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl]amine

Thomas J Fleck, William W McWhorter Jr, Richard N DeKam, Bruce A Pearlman

J Org Chem. 2003 Dec 12;68(25):9612-7.

PMID: 14656085

Abstract:

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).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1219810168	1S,3R-RSL 3		1219810-16-8	Price

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