1,4-Cyclohexadiene → (R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-one

HRID 332643

Reaktionsgleichung

Reaktionsgleichung von HRID 332643
[N:1]([CH2:4][C@@H:5]([C:14]1[CH:23]=[CH:22][C:21]([O:24]CC2C=CC=CC=2)=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18](=[O:32])[NH:19]2)[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[N+]=[N-].C1CC=CCC=1>[Pd].C(O)C>[NH2:1][CH2:4][C@@H:5]([C:14]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18](=[O:32])[NH:19]2)[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Komponenten

5

Edukt 2

HCID 123431,4-CyclohexadieneHCID 58505233(R)-5-(2-Azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one

Produkt 1

HCID 59023604(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-oneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To an ice-cooled suspension of (R)-5-(2-azido-1-(tert-butyldimethylsilyloxy)-ethyl)-8-(benzyloxy)quinolin-2(1H)-one (5.77 g, 12.8 mmol) and palladium on activated charcoal (5.8 g, 10% w/w wet) in ethanol (50 mL), 1,4-cyclohexadiene (12.0 mL, 126 mmol) was added dropwise. After stirring at this temperature for 30 minutes, the coolant was removed and replaced with a water bath at 30° C. The reaction was stirred at this temperature for 1 hour. The suspension was filtered and the filter cake washed with further ethanol. The filtrate was evaporated under reduced pressure to dryness. The resulting solid was suspended in acetonitrile and stirred for 1 hour. The suspension was filtered and the resulting solid air-dried under vacuum to afford the title compound (2.90 g, 87%).

Aufarbeitung

  1. additionwas added dropwise
  2. customthe coolant was removed
  3. customreplaced with a water bath at 30° C
  4. stirringThe reaction was stirred at this temperature for 1 hour
  5. filtrationThe suspension was filtered
  6. washthe filter cake washed with further ethanol
  7. customThe filtrate was evaporated under reduced pressure to dryness
  8. stirringstirred for 1 hour
  9. filtrationThe suspension was filtered
  10. customthe resulting solid air-dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-359cca3e08c349849edd45fa4617420c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877774B2

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