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N-methylative aziridine ring opening and the synthesis of (S)-3-methylamino-3-[(R)-pyrrolidin-3-yl]propanenitrile
- Jung, Jae-Hoon;
- Kim, Seunghee;
- Eum, Heesung;
- Lee, Won Koo;
- Ha, Hyun-Joon
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7초록
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.
키워드
Aziridine; Ring opening; PF-00951966; Pyrrolidine; Conjugate addition; NICKEL HYDROGENATION CATALYST; SODIUM-BOROHYDRIDE; ASYMMETRIC-SYNTHESIS; NITRO-COMPOUNDS; ALIPHATIC NITROCOMPOUNDS; ENANTIOMERICALLY PURE; CONJUGATE ADDITION; ETHANOL SOLUTION; REDUCTION; NITROMETHANE
- 제목
- N-methylative aziridine ring opening and the synthesis of (S)-3-methylamino-3-[(R)-pyrrolidin-3-yl]propanenitrile
- 저자
- Jung, Jae-Hoon; Kim, Seunghee; Eum, Heesung; Lee, Won Koo; Ha, Hyun-Joon
- 발행일
- 2017-10-12
- 유형
- Article
- 저널명
- Tetrahedron
- 권
- 73
- 호
- 41
- 페이지
- 5993 ~ 5999