Sodium cyanoborohydride → HCID 11256259, Verbindung

HRID 2238602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2238602
Cl.[CH3:2][NH:3][C:4](=[O:8])[C@H:5]([CH3:7])[NH2:6].C([BH3-])#N.[Na+].[C:13]1([CH2:19][CH2:20][CH:21]2[C:25]3[CH:26]=[C:27]([CH:30]=O)[CH:28]=[CH:29][C:24]=3[O:23][CH2:22]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[CH2:20]([CH:21]1[C:25]2[CH:26]=[C:27]([CH2:30][NH:6][CH:5]([CH3:7])[C:4]([NH:3][CH3:2])=[O:8])[CH:28]=[CH:29][C:24]=2[O:23][CH2:22]1)[CH2:19][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 18595779(2S)-2-amino-N-methylpropanamide hydrochlorideHCID 57445526HCID 57445526, Verbindung

Produkt 1

HCID 11256259HCID 11256259, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of N-methyl-alaninamide hydrochloride (0.50 g, 3.61 mmol) in methanol (10 ml), in the presence of molecular sieves (1.00 g), sodium cyanoborohydride (0.36 g, 5.69 mmol) and a solution of 3-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-carboxaldehyde (0.90 g, 3.61 mmol) in methanol (10 ml) were added at room temperature. The reaction mixture was kept under stirring and an argon atmosphere for 12 h. Then, the solvent was evaporated under vacuum and the residue was purified by flash chromatography on silica gel (ethyl acetate/methanol=98/2) affording 0.93 g of title compound (77% yield).

Aufarbeitung

  1. customThen, the solvent was evaporated under vacuum
  2. customthe residue was purified by flash chromatography on silica gel (ethyl acetate/methanol=98/2)

Quellen und Nachweise

ORD-Eintrag
ord-5165846ba05a47a0b3d46687e1b736ea
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718815B2

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