Water → 5-Bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole

HRID 1681634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1681634
[CH3:1][N:2]1[CH:6]2[N:7]([CH3:14])[C:8]3[C:13]([C:5]2([CH3:15])[CH2:4][CH2:3]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.N1C=CC=CC=1.[BrH:22].[NH+]1C=CC=CC=1.O>C(Cl)Cl>[Br:22][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:14])[CH:6]1[N:2]([CH3:1])[CH2:3][CH2:4][C:5]21[CH3:15]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 13000841HCID 13000841, VerbindungHCID 21226041Pyridinium hydrobromide

Produkt 1

HCID 197825615-Bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a chilled (0° C.) solution of 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole (1.41 g) in methylene chloride (20 ml) was added pyridine (1.41 ml) under an atmosphere of N2. Solid pyridinium hydrobromide perbromide (2.23 g) was added with stirring to the mixture and the resulting solution was maintained at 0° C. for 1 hour. The mixture was poured into water (100 ml) and the aqueous and organic phases separated. The organic phase was washed twice with 50 ml portions of brine and 50 ml portions of saturated sodium bicarbonate and then with 50 ml of brine. After drying the organic phase over Na2SO4 and filtering, the solvent was removed under reduced pressure. The resulting oil was purified using column chromatography on silica gel with 10% methanol in ethyl acetate as eluent. The appropriate fractions were combined, evaporated and repurified using column chromatography on silica gel with 5% methanol in ethyl acetate as eluant to afford 1.5 g of 5-bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indole, as an oil.

Aufarbeitung

  1. customthe aqueous and organic phases separated
  2. washThe organic phase was washed twice with 50 ml portions of brine and 50 ml portions of saturated sodium bicarbonate
  3. dry with materialAfter drying the organic phase over Na2SO4
  4. filtrationfiltering
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting oil was purified
  7. customevaporated
  8. customrepurified

Quellen und Nachweise

ORD-Eintrag
ord-8fe5de5a4d784a4692e4fea58d9345a5
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05173497

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