4-(((Tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile → 3-(aminomethyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methylpyridin-2(1H)-one

HRID 1616436Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616436
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[NH:13][C:12](=[O:17])[C:11]=1[C:18]#[N:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H][H]>CO.N.[Ni]>[NH2:19][CH2:18][C:11]1[C:12](=[O:17])[NH:13][C:14]([CH3:16])=[CH:15][C:10]=1[CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Komponenten

6

Edukt 2

HCID 682948094-(((Tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrileHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 682947603-(aminomethyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methylpyridin-2(1H)-oneAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 222AmmoniaLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (5.5 g, 19.7 mmol) in methanol (100 mL) and ammonia (30 mL) was added Raney nickel (quantitative) and the reaction mixture was stirred in presence of hydrogen under balloon pressure for 14 h. On completion, reaction mixture was filtered through celite and washed with methanol. Removal of the solvent under reduced pressure afforded the desired compound (3.5 g, 63%).

Aufarbeitung

  1. customOn completion, reaction mixture
  2. filtrationwas filtered through celite
  3. washwashed with methanol
  4. customRemoval of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-80fb6c174169404a808252e5a23d91c4
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765732B2

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