Methyl iodide → tert-Butyl 9-methyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

HRID 2301077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2301077
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:23]I>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH3:23])[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18377349tert-butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Produkt 1

HCID 10989795tert-Butyl 9-methyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylateAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 66 mg (1.65 mmol) portion of sodium hydride was added to 10 ml of DMF solution containing 300 mg (1.10 mmol) of 2-t-butoxycarbonyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole and stirred at room temperature for 30 minutes, and then 103 μl (1.65 mmol) of methyl iodide were added thereto and stirred overnight at room temperature. The reaction solution was extracted with ethyl acetate and washed with water. After drying (Na2SO4), the solvent was removed by evaporation under a reduced pressure and the resulting oil was purified by a silica gel column chromatography (60 cc; elution by ethyl acetate-hexane=1:5) to obtain 200 mg of the title compound (63% in yield).

Aufarbeitung

  1. stirringstirred overnight at room temperature
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialAfter drying (Na2SO4)
  5. customthe solvent was removed by evaporation under a reduced pressure
  6. customthe resulting oil was purified by a silica gel column chromatography (60 cc; elution by ethyl acetate-hexane=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-e361cb1a865548fdbcbbe2bca783fb82
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498251B1

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