Sodium Hydroxide → 3,4-Dihydro-1H-beta-carboline-2,9-dicarboxylic acid 2-tert-butyl ester 9-(2,2,2-trichloro-ethyl) ester

HRID 992414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 992414
[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].[Cl:21][C:22]([Cl:29])([Cl:28])[CH2:23][O:24][C:25](Cl)=[O:26].[OH-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Cl:21][C:22]([Cl:29])([Cl:28])[CH2:23][O:24][C:25]([N:11]1[C:10]2[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:20][CH2:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:26]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 18377349tert-butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Produkt 1

HCID 698941943,4-Dihydro-1H-beta-carboline-2,9-dicarboxylic acid 2-tert-butyl ester 9-(2,2,2-trichloro-ethyl) esterAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1,3,4,9-Tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester (7.68 g), 2,2,2-trichloroethylchloroformate (5.8 ml), sodium hydroxide (2.8 g) and tetrabutylammonium iodide (catalytic) in dichloromethane (100 ml) were stirred under nitrogen at room temperature for 5 h. The mixture was diluted with dichloromethane (100 ml), washed with water (150 ml) and brine (100 ml), then dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed (SiO2, 1% methanol in dichloromethane) to give the title compound (3.53 g, 28%) as a yellow foam.

Aufarbeitung

  1. washwashed with water (150 ml) and brine (100 ml)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customThe residue was chromatographed (SiO2, 1% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-de1e37f8d1ba453f964b7a769b225baa
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06469020B2

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