Phenyl isocyanate → HCID 68545203, Verbindung

HRID 1445715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1445715
[CH3:1][O:2][C:3]([C@@H:5]1[CH:14]=[C:13]2[C@@H:8]([CH2:9][C:10]3[C:11]4[C:18]([NH:19][CH:20]=3)=[CH:17][CH:16]=[CH:15][C:12]=42)[NH:7][CH2:6]1)=[O:4].[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl.CO.C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:5]1[CH:14]=[C:13]2[C@@H:8]([CH2:9][C:10]3[C:11]4[C:18]([NH:19][CH:20]=3)=[CH:17][CH:16]=[CH:15][C:12]=42)[N:7]([C:28](=[O:29])[NH:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:6]1)=[O:4]

Komponenten

5

Edukt 2

HCID 7672Phenyl isocyanateHCID 68539805HCID 68539805, Verbindung

Produkt 1

HCID 68545203HCID 68545203, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

To a 100 ml round-bottom flask containing a solution of (6aR,9R)-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid methyl ester (0.89, 2.98 mmol) in dichloromethane (20 ml) is added phenylisocyanate (0.45 ml, 4.5 mmol, 1.5 eq.). The reaction mixture is stirred at room temperature for 16 hours by which time TLC in 10% methanol/DCM showed conversion of starting material to give product as a mixture of diastereomers. The volatiles are concentrated in vacuo and purified directly using Normal Phase Flash column chromatography (Biotage Flash 40, 90 g cartridge) using 30% ethyl acetate/hexane to isolate the product as a 1:1 diastereomeric mixture.

Aufarbeitung

  1. customto give product
  2. additionas a mixture of diastereomers
  3. concentrationThe volatiles are concentrated in vacuo
  4. custompurified directly
  5. customto isolate the product as a 1:1 diastereomeric mixture

Quellen und Nachweise

ORD-Eintrag
ord-34889c7dd4aa4e4a8a320f444e71596c
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666877B2

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