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N-methylative aziridine ring opening and the synthesis of (S)-3-methylamino-3-[(R)-pyrrolidin-3-yl]propanenitrile

조회수 : 43 등록일 : 2017.11.16 00:00

저자 : Lee, WK (Lee, Won Koo)
출처 : TETRAHEDRON
출판일 : 2017.10.12


N-methylative aziridine ring opening and the synthesis of (S)-3-methylamino-3-[(R)-pyrrolidin-3-yl]propanenitrile


Jung, JH (Jung, Jae-Hoon)1 ] Kim, S (Kim, Seunghee)1 ] Eum, H (Eum, Heesung)1 ] Lee, WK (Lee, Won Koo)2 ] Ha, HJ (Ha, Hyun-Joon)1 ]


[ 1 ] Hankuk Univ Foreign Studies, Dept Chem, Yongin 17035, Gyeonggi Do, South Korea
[ 2 ] Sogang Univ, Dept Chem, Seoul 04107, South Korea



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-yllaziridine. The starting compound was elaborated from stereoselective conjugate addition of nitromethane to (R)-aziridine-2-y1 acrylate followed by selective reduction without breaking the aziridine ring. (C) 2017 Elsevier Ltd. All rights reserved.






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