HCID 10362064, Verbindung → HCID 19026196, Verbindung

HRID 1033507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1033507
[CH3:1][Li].[C:3]1([CH2:9][O:10][NH:11][C:12]2([CH3:30])[CH2:21][CH2:20][CH2:19][C:18]3[N:17]=[C:16]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:15]=[CH:14][C:13]2=3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCCC1>[C:3]1([CH2:9][O:10][N:11]([CH3:1])[C:12]2([CH3:30])[CH2:21][CH2:20][CH2:19][C:18]3[N:17]=[C:16]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:15]=[CH:14][C:13]2=3)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 10362064HCID 10362064, VerbindungHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 19026196HCID 19026196, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyllithium (1.4M in diethyl ether, 37.7 ml) was added dropwise over 20 min to a solution of N,2-bis(phenylmethoxy)-5,6,7,8-tetrahydro-5-methyl--5-quinolinamine (18.1 g) and tetrahydrofuran (20 ml) at -78° C. The mixture was allowed to warm to room temperature over 2 hrs and was stirred at room temperature for an additional 1 hr. The solution was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate, filtered, and the filtrate was concentrated. The residue was purified by high performance liquid chromatography (silica gel, elution with ethyl acetate-hexanes) to provide 12.3 g (65%) of product.

Aufarbeitung

  1. customThe solution was quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by high performance liquid chromatography (silica gel, elution with ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4ee1f4fedbc74b809905c714e8678d00
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05310914

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