tert-butyl (2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]aziridine-1-carboxylate → Tert-Butyl (1S)-2-(3,5-difluorophenyl)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethylcarbamate

HRID 132805노트

반응식

HRID 132805 반응식
[CH3:1][C:2]1([CH3:17])[O:6][C@@H:5]([C@@H:7]2[CH2:9][N:8]2[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4][O:3]1.[F:18][C:19]1[CH:20]=[C:21]([Mg]Br)[CH:22]=[C:23]([F:25])[CH:24]=1>C1COCC1.CSC.[Cu](Br)Br>[F:18][C:19]1[CH:20]=[C:21]([CH2:9][C@H:7]([NH:8][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[C@H:5]2[CH2:4][O:3][C:2]([CH3:1])([CH3:17])[O:6]2)[CH:22]=[C:23]([F:25])[CH:24]=1

참가 물질

5

반응물 2

HCID 58802797tert-butyl (2S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]aziridine-1-carboxylateHCID 178505930HCID 178505930, 화합물

생성물 1

HCID 71091996Tert-Butyl (1S)-2-(3,5-difluorophenyl)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethylcarbamate

시약·촉매·용매 2

HCID 11403411Copper bromide-dimethyl sulfide촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

BOC-Aziridine (21), copper bromide-dimethyl sulfide (0.15 eq.), and THF were cooled to −20° and (3,5-difluorophenyl)magnesium bromide (1.25 eq.) in THF was added. The reaction was allowed to warm to 200 and stir overnight. The reaction was extracted and the solvent removed to afford the crude product (26) as a syrup.

후처리

  1. temperatureto warm to 200
  2. extractionThe reaction was extracted
  3. customthe solvent removed

출처 및 근거

ORD 기록
ord-9f7a50fe966a4effb10fd8fb00c3f23c
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388118B2

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