Acetic Acid → HCID 14181063, Verbindung

HRID 465407Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 465407
C([BH3-])#N.[Na+].[CH3:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[CH2:15][C:14](=O)[CH2:13][CH2:12]2.[NH2:18][CH2:19][CH2:20][N:21](CC)[C:22](=[O:24])[O-:23].[C:27](O)(=O)[CH3:28]>>[CH2:27]([O:23][C:22]([NH:21][CH2:20][CH2:19][NH:18][CH:14]1[CH2:13][CH2:12][C:11]2[C:16](=[C:7]([O:6][CH3:5])[CH:8]=[CH:9][CH:10]=2)[CH2:15]1)=[O:24])[CH3:28]

Komponenten

5

Edukt 4

HCID 176Acetic AcidHCID 41360218-Methoxy-2-tetraloneHCID 5003444Sodium cyanoborohydrideHCID 21616286HCID 21616286, Verbindung

Produkt 1

HCID 14181063HCID 14181063, VerbindungAusbeute 46,2 %

Versuchsvorschrift

10.0 g (159 mmol) of sodium cyanoborohydride were added to the solution of 7.00 g (40 mmol) of 8-methoxy-2-tetralone, 8.00 g (61 mmol) of N-(2-aminoethyl)ethylcarbamate and 9.60 g (160 mmol) of glacial acetic acid at 0° C. After 15 hours at room temperature, the mixture was concentrated, taken up in tert.-butyl methyl ether, and treated with water. The pH of the aqueous phase was adjusted to 10 using sodium hydroxide solution. The mixture was stirred vigorously for 30 minutes. The organic phase was separated off, and the aqueous phase was extracted thoroughly with the last-mentioned solvent. Drying the organic phase and concentrating supplied an oil, which was purified by chromatography on silica gel (toluene/ethanol gradients with addition of 0.3% triethylamine). 5.40 g (46%) of the pure title compound were obtained as a brownish oil.

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. additiontreated with water
  3. customThe organic phase was separated off
  4. extractionthe aqueous phase was extracted thoroughly with the last-mentioned solvent
  5. customDrying the organic phase
  6. concentrationconcentrating
  7. customwas purified by chromatography on silica gel (toluene/ethanol gradients with addition of 0.3% triethylamine)

Quellen und Nachweise

ORD-Eintrag
ord-da338381bef947489b7328cab68857bf
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153225

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