(R)-(+)-3-Chlorostyrene oxide → 3-{(2 R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1H-indole-7-carboxylic acid diethylamide

HRID 1351936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1351936
[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C@H:16]([NH2:18])[CH3:17])=[O:5])[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C@H:25]1[O:27][CH2:26]1>C(#N)C>[CH2:19]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C@H:16]([NH:18][CH2:26][C@@H:25]([C:24]1[CH:28]=[CH:29][CH:30]=[C:22]([Cl:21])[CH:23]=1)[OH:27])[CH3:17])=[O:5])[CH3:20]

Komponenten

4

Edukt 2

HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 69457261(R)-3-(2-aminopropyl)-1H-indole-7-carboxylic acid diethylamide

Produkt 1

HCID 694562293-{(2 R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1H-indole-7-carboxylic acid diethylamideAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of (R)-3-(2-aminopropyl)-1H-indole-7-carboxylic acid diethylamide (1.30 g, 4.76 mmol) and (R)-(+)-3-chlorostyrene oxide (1.21 mL, 9.52 mmol) in acetonitrile (15 mL) is refluxed for 10 hours. After cooling, the mixture is concentrated and the residue is purified by silica gel column chromatography (a saturated ammonia solution in chloroform) to give the desired 3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-7-carboxylic acid diethylamide (0.79 g, yield: 39%).

Aufarbeitung

  1. temperatureis refluxed for 10 hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. customthe residue is purified by silica gel column chromatography (a saturated ammonia solution in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-6f6f286a711e44f0a28666cc9f324937
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217724B2

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