Acetonitrile → HCID 59496607, Verbindung

HRID 449529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449529
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2.Br[CH2:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[C:24]#[N:25].C(#N)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C>[C:24]([C:23]1[CH:22]=[C:21]([CH:28]=[CH:27][CH:26]=1)[CH2:20][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)#[N:25]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 10538586tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

Produkt 1

HCID 59496607HCID 59496607, VerbindungAusbeute 109,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.025 g, 0.10 mmol) was combined with 3-(bromomethyl)benzonitrile (Aldrich, 145610) (0.029 g, 0.15 mmol), acetonitrile (2.0 mL) and cesium carbonate (0.065 g, 0.20 mmol) and was stirred at r.t. overnight. This was diluted with ethyl acetate, filtered to remove the solids and concentrated under reduced pressure to give crude tert-butyl 5-(3-cyanobenzyloxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.040 g) as a semisolid. Analytical LCMS (M+Na)+: m/z=387.0.

Aufarbeitung

  1. filtrationfiltered
  2. customto remove the solids
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5c3f7cf940cc47f3bc97f9b6bd673ac2
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481732B2

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