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 132805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132805
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11403411Copper bromide-dimethyl sulfideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9f7a50fe966a4effb10fd8fb00c3f23c
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388118B2

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