Benzyl Bromide → 9-benzyl-2-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

HRID 1106917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1106917
[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:23]([N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH2:19][CH2:20][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C:10]1=2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18377349tert-butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Produkt 1

HCID 183772769-benzyl-2-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole(2.96 g, 10.9 mmol) in dry DMF (15 ml) was added dropwise to a slurry of sodium hydride (60% dispersion in oil/479 mg, 12.0 mmol) in dry DMF (15 ml) maintained under nitrogen at room temperature. After stirring for 45 minutes at room temperature benzyl bromide (1.3 ml, 10.9 mmol) was added dropwise. The reaction was stirred for a further 2 hours, diluted with ethyl acetate (75 ml), washed with brine (2×80 ml) and dried (MgSO4). Filtration and evaporation of the solvent gave the crude product which was purified by chromatography on silica gel with ethyl acetate-hexane (2:7) as eluant. (3.68 g, 92%).

Aufarbeitung

  1. additionwas added dropwise
  2. washwashed with brine (2×80 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-2aa3759fab0a400384024f07123be9cb
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057311

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