Water → HCID 14994381, Verbindung

HRID 846582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 846582
[NH2:1][C:2]1[C:7]([C:8](OCC)=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:5]([C:20]([O:22][CH3:23])=[O:21])=[C:4]([CH:24]([CH3:26])[CH3:25])[N:3]=1.O>C1(C)C=CC=CC=1.O1CCCC1>[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[C:5]([C:20]([O:22][CH3:23])=[O:21])=[C:4]([CH:24]([CH3:26])[CH3:25])[N:3]=1

Komponenten

5

Edukt 2

HCID 962WaterHCID 14994380Amino-3-ethoxycarbonyl-4-(4-fluorophenyl)-6-isopropyl-5-methoxycarbonyl-pyridine

Produkt 1

HCID 14994381HCID 14994381, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

100 ml (0.35 mol) of a 3.5M solution of sodium bis-(2-methoxy-ethoxy)-dihydroaluminate in toluene are initially introduced under argon into 100 ml of tetrahydrofuran p.a. 63 g (175 mmol) of the compound from Example III dissolved in 700 ml of tetrahydrofuran are added dropwise and the mixture is subsequently stirred at 30° C. for 1 h. 2 l of water are cautiously added dropwise. The phases are separated and the aqueous phase is washed twice with 700 ml of ethyl acetate. The combined organic phases are washed with 500 ml of saturated sodium chloride solution and dried using sodium sulphate. The solution is filtered and concentrated in vacuo. The residue is chromatographed in a column (φ 6 cm) on 400 g of silica gel 230-400 mesh using petroleum ether/ethyl acetate (1:1). The eluate is concentrated in vacuo and the residue is thoroughly stirred in ether/petroleum ether.

Aufarbeitung

  1. additionare added dropwise
  2. customThe phases are separated
  3. washthe aqueous phase is washed twice with 700 ml of ethyl acetate
  4. washThe combined organic phases are washed with 500 ml of saturated sodium chloride solution
  5. customdried
  6. filtrationThe solution is filtered
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed in a column (φ 6 cm) on 400 g of silica gel 230-400 mesh
  9. concentrationThe eluate is concentrated in vacuo
  10. stirringthe residue is thoroughly stirred in ether/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-13bb54d256b045ba8d39f0f62e699e4b
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05137881

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