Synthesis of N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl}amine
1
Early Process Research and Development, Medicinal Chemistry Research, and Chemical Research and Development, Pfizer, Inc., Kalamazoo, Michigan 49001
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Publication type: Journal Article
Publication date: 2003-11-19
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
14656085
Organic Chemistry
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).
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40
Total citations:
40
Citations from 2024:
1
(2.5%)
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GOST
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Fleck T. J. et al. Synthesis of N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl}amine // Journal of Organic Chemistry. 2003. Vol. 68. No. 25. pp. 9612-9617.
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Fleck T. J., Mcwhorter W. W., Dekam R. N., Pearlman B. A. Synthesis of N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl}amine // Journal of Organic Chemistry. 2003. Vol. 68. No. 25. pp. 9612-9617.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo0349633
UR - https://doi.org/10.1021/jo0349633
TI - Synthesis of N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl}amine
T2 - Journal of Organic Chemistry
AU - Fleck, Thomas J
AU - Mcwhorter, William W
AU - Dekam, Richard N
AU - Pearlman, Bruce A
PY - 2003
DA - 2003/11/19
PB - American Chemical Society (ACS)
SP - 9612-9617
IS - 25
VL - 68
PMID - 14656085
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2003_Fleck,
author = {Thomas J Fleck and William W Mcwhorter and Richard N Dekam and Bruce A Pearlman},
title = {Synthesis of N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl}amine},
journal = {Journal of Organic Chemistry},
year = {2003},
volume = {68},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/jo0349633},
number = {25},
pages = {9612--9617},
doi = {10.1021/jo0349633}
}
Cite this
MLA
Copy
Fleck, Thomas J., et al. “Synthesis of N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl}amine.” Journal of Organic Chemistry, vol. 68, no. 25, Nov. 2003, pp. 9612-9617. https://doi.org/10.1021/jo0349633.