Chlorosuccinimide → 1-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazole

HRID 1634715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634715
[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.[Cl:19]N1C(=O)CCC1=O>CN(C=O)C>[Cl: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.[Cl:19][C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:6]=1[O:5][CH2:4][C@@H:2]1[CH2:3][O:1]1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Komponenten

5

Edukt 2

HCID 31398ChlorosuccinimideHCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazole

Produkt 2

HCID 590329461-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazoleHCID 590329593-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-[(2S)-oxiranylmethoxy]-9H-carbazole (0.50 g, 2.09 mmol) and N-chlorosuccinimide (0.280 g, 2.09 mmol) in 5 mL dry 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 (methylene chloride-hexane-1:1) afforded 0.10 g of the title compound plus 0.50 g of 3-Chloro-4-[(2S)-oxiranylmethoxy]-9H-carbazole.

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 (methylene chloride-hexane-1:1)

Quellen und Nachweise

ORD-Eintrag
ord-420bbba7dd7e4683b5048af95a46fd4b
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506901B2

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