Water → (R)-2-[1-(2,6-Dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-3-ethoxymethyl-1,2,3,4-tetrahydro-isoquinoline

HRID 1740115Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1740115
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([N:14]2[C:18]([CH2:19][CH3:20])=[C:17]([CH2:21][N:22]3[C@@H:31]([CH2:32][O:33][CH2:34][CH3:35])[CH2:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:23]3)[C:16]([CH2:36][CH3:37])=[N:15]2)=[C:9]([CH3:38])[CH:8]=1.O>O1CCCC1>[CH3:13][C:11]1[CH:12]=[CH:7][CH:8]=[C:9]([CH3:38])[C:10]=1[N:14]1[C:18]([CH2:19][CH3:20])=[C:17]([CH2:21][N:22]2[C@@H:31]([CH2:32][O:33][CH2:34][CH3:35])[CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23]2)[C:16]([CH2:36][CH3:37])=[N:15]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 53638919(R)-2-[1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-3-ethoxymethyl-1,2,3,4-tetrahydro-isoquinolineHCID 178418339Butyllithium

Produkt 1

HCID 53917900(R)-2-[1-(2,6-Dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-3-ethoxymethyl-1,2,3,4-tetrahydro-isoquinolineAusbeute 60,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of n-butyl lithium (2.5 M hexane solution; 0.028 ml, 0.071 mmol) chilled to -78° C., a solution of (R)-2-[1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-3-ethoxymethyl-1,2,3,4-tetrahydro-isoquinoline (33 mg, 0.065 mmol) in anhydrous tetrahydrofuran (0.1 ml) was added dropwise. After stirring at -78° C. for 10 minutes, water (0.1 ml) was added. The resulting mixture was warmed to room temperature and stirred for 20 minutes. The reaction was quenched by addition of aqueous ammonium chloride (1 ml), and then extracted with ethyl acetate/water (5 ml of each). The separated organic extract was washed with an equal volume solution of aqueous ammonium chloride, dried over anhydrous sodium sulfate and concentrated in vacuo to afford a yellow oil (17 mg). Flash chromatography (silica gel, 40 micron mesh; elution with ethyl acetate/hexane=1:5 in volume) afforded the title compound (2 mg) as a yellow oil.

Aufarbeitung

  1. temperatureThe resulting mixture was warmed to room temperature
  2. stirringstirred for 20 minutes
  3. customThe reaction was quenched by addition of aqueous ammonium chloride (1 ml)
  4. extractionextracted with ethyl acetate/water (5 ml of each)
  5. extractionThe separated organic extract
  6. washwas washed with an equal volume solution of aqueous ammonium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3050971fb0c84c5ab82d638f0d6425b0
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05968944

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