Reaktion #1070819

Reaktionsgleichung

1-(2-methoxy-phenyl)-ethanone

N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

AcOH

NaBH(OAc)3

→

desired product

Ausbeute 134.8%

2-hydroxy-pyridine-3-carbaldehyde

Ausbeute 134.8%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigePurification of the crude light yellow foam to (267 mg) by column chromatography on silica gel (100:1:1-CH2Cl2:MeOH:NH4OH)

Vorschrift

To a stirred solution of 1-(2-methoxy-phenyl)-ethanone (69 μL, 0.50 mmol), N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (200 mg, 0.50 mmol) and AcOH (0.10 mL, 1.4 mmol) in THF (5 mL) was added NaBH(OAc)3 and the mixture was stirred at room temperature for 48 hours. Purification of the crude light yellow foam to (267 mg) by column chromatography on silica gel (100:1:1-CH2Cl2:MeOH:NH4OH) followed by radial chromatography on silica gel (100:1:1-CH2Cl2:MeOH:NH4OH) afforded the desired product (83 mg, 27%) as a white foam.

Quelle