Potassium Iodide → 2-(4'-Fluoro-4-biphenylylmethyl)-6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

HRID 257070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 257070
[CH3:1][O:2][CH:3]([O:17][CH3:18])[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[NH:11][CH2:10][CH2:9]2.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32]Br)=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.[H-].[Na+].[I-].[K+]>CN(C=O)C.O>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][N:11]3[CH2:10][CH2:9][C:8]4[C:13](=[CH:14][CH:15]=[C:6]([O:5][CH2:4][CH:3]([O:2][CH3:1])[O:17][CH3:18])[CH:7]=4)[C:12]3=[O:16])=[CH:28][CH:27]=2)=[CH:24][CH:25]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 189638634-(Bromomethyl)-4'-fluoro-1,1'-biphenylHCID 189638836-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 189639412-(4'-Fluoro-4-biphenylylmethyl)-6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline (5.79 g, 23.05 mmol) and 4'-fluoro-4-biphenylylmethyl bromide (9.16 g, 34.57 mmol), in DMF (100 ml) is added sodium hydride (1.1 g, 27.5 mmol) and a catalytic amount of potassium iodide. The reaction mixture is stirred for 2 hours at room temperature and is subsequently diluted with H2O (500 ml). The mixture is then extracted with EtOAc (2×300 ml). The combined EtOAc portions are washed with saturated NaCl solution (600 ml), dried over MgSO4, and concentrated in vacuo and washed with hexanes to yield the acetal, 2-(4'-fluoro-4-biphenylylmethyl)-6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Aufarbeitung

  1. extractionThe mixture is then extracted with EtOAc (2×300 ml)
  2. washThe combined EtOAc portions are washed with saturated NaCl solution (600 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. washwashed with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7564cb1984e942478228cdf43ac8475e
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05260316

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