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| Type |
Poster Presentation |
| Area |
Organic Chemistry |
| Room No. |
Event Hall |
| Time |
4월 19일 (목요일) 11:00~12:30 |
| Code |
ORGN.P-335 |
| Subject |
N-methylative aziridine ring opening and the synthesis of (S)-3-methylamino-3-[(R)-pyrrolidin-3-yl]propanenitrile
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| Authors |
Sangyun Na, Won Koo Lee1, Hyun-Joon Ha*
Department of Chemistry, Hankuk University of Foreign Studies, Korea
1Department of Chemistry, Sogang University, Korea
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| Abstract |
The preparation of (S)-3-methylamino-3-[(R)-pyrrolidin-3-yl]propanenitrile (1), a key fragment of fluoroquinolone antibiotic PF-00951966 and others was achieved by N-methylative aziridine ring opening, addition of methyl group at the ring nitrogen, and ring-opening via a cyanide nucleophile in a single operation starting from bicyclic (R)-2-[(R)-pyrrolidine-3-yl]aziridine. The starting compound was elaborated from stereoselective conjugate addition of nitromethane to (R)-aziridine-2-yl acrylate followed by selective reduction without breaking the aziridine ring.
References:
1. J. Lee, JE. Lee, HJ. Ha, SI. Son, WK. Lee. Tetrahedron Lett. 2015, 56, 856-858.
2. DH. Yoon, P. Kang, WK Lee, Y. Kim, HJ. Ha. Org Lett. 2012, 14, 429-431.
3. MS. Lall, G. Hoge, TP. Tran, et al. J Org Chem. 2012, 77, 4732-4739.
4. J-H. Jung, S Kim, H. Eum, WK. Lee, HJ. Ha. Tetrahedron. 2017, 73(41), 5993-5999.
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| E-mail |
ssang0520@gmail.com |
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121st General Meeting of the KCS