N-bromobutanimide → 1-bromo-4-[(2S)-oxiranylmethoxy]-9H-carbazole

HRID 1634714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634714
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[Br:19]N1C(=O)CCC1=O>CN(C)C=O>[Br:19][C:9]1[C:10]2[NH:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[C:6]([O:5][CH2:4][C@@H:2]2[CH2:3][O:1]2)=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazole

Produkt 1

HCID 590329641-bromo-4-[(2S)-oxiranylmethoxy]-9H-carbazoleAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-[(2S)-oxiranylmethoxy]-9H-carbazole (0.750 g, 3.13 mmol) and N-bromosuccinimide (0.57 g, 3.2 mmol) in 10 mL dry dimethylformamide (DMF) was stirred at ambient temperature for 48 hours. The reaction mixture was partitioned with EtOAc and H2O. The organic phase was washed with H2O and dried with Na2SO4. The solvent was removed (rotovap) and the residue purified by flash chromatography (hexane-EtOAc 5:1) afforded 0.10 g of the title compound.

Aufarbeitung

  1. customThe reaction mixture was partitioned with EtOAc and H2O
  2. washThe organic phase was washed with H2O
  3. dry with materialdried with Na2SO4
  4. customThe solvent was removed (rotovap)
  5. customthe residue purified by flash chromatography (hexane-EtOAc 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-6a6055ec7e90482aac559e9c310f8a1d
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506901B2

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