diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylate → Ethyl 1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate

HRID 1710449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710449
C([O:3][C:4]([C:6]1[N:7]([CH2:20][C:21]#[N:22])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]=2)=O)C.[H][H]>CCO.O=[Pt]=O>[CH2:18]([O:17][C:15]([C:10]1[CH:11]=[CH:12][C:13]2[CH:14]=[C:6]3[C:4](=[O:3])[NH:22][CH2:21][CH2:20][N:7]3[C:8]=2[CH:9]=1)=[O:16])[CH3:19]

Komponenten

5

Edukt 2

HCID 58767564diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 68506420Ethyl 1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylateAusbeute 109,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To 1-cyanomethyl-1H-indole-2,6-dicarboxylic acid diethyl ester (500 mg, 1.66 mmol) in 20 mL of absolute EtOH was added PtO2 (Adams' catalyst). The reaction mixture was hydrogenated at 50 psi of hydrogen overnight. The reaction mixture was filtered through a pad of diatomaceous earth, the solid cake was washed with dichloromethane several times. The solvent was evaporated to dryness to give 468 mg of 1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid ethyl ester as a light yellow solid.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. washthe solid cake was washed with dichloromethane several times
  3. customThe solvent was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3f22195600214fb980c219b22df37b03
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790712B2

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