5-Nitroindole → 1-[(5-nitro-1H-indol-3-yl)methyl]-4-propylpyrrolidin-2-one

HRID 1896347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896347
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].O[CH2:14][N:15]1[CH2:19][CH:18]([CH2:20][CH2:21][CH3:22])[CH2:17][C:16]1=[O:23]>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:14][N:15]1[CH2:19][CH:18]([CH2:20][CH2:21][CH3:22])[CH2:17][C:16]1=[O:23])([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 225235-NitroindoleHCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-one

Produkt 1

HCID 159794491-[(5-nitro-1H-indol-3-yl)methyl]-4-propylpyrrolidin-2-oneAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 5-nitro-1H-indole x3 (100 mg, 1 eq, 0.62 mmol), 1-(hydroxymethyl)-4-propylpyrrolidin-2-one x2 (108.27 mg, 1 eq, 0.62 mmol), paratoluenesulfonic acid (11 mg, 0.1 eq, 0.062 mmol) in 5 ml of toluene is refluxed for 4 hours. After cooling to room temperature, the solvent is removed under reduced pressure and the crude product is purified by preparative chromatography on reverse phase (gradient: H2O/CH3CN/TFA: 95/5/0.1 (v/v/v) to 5/95/0.1 (v/v/v)) affording 1-[(5-nitro-1H-indol-3-yl)methyl]-4-propylpyrrolidin-2-one 148 as a colorless oil.

Aufarbeitung

  1. customthe solvent is removed under reduced pressure
  2. customthe crude product is purified by preparative chromatography on reverse phase (gradient: H2O/CH3CN/TFA: 95/5/0.1 (v/v/v) to 5/95/0.1 (v/v/v))

Quellen und Nachweise

ORD-Eintrag
ord-88b05393e29a4019a19423abbc23cbd4
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518943B2

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