[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:10]([CH2:27][CH2:28][CH3:29])[CH:11]([CH2:17][C:18]1[C:26]2[N:25]=[CH:24][NH:23][C:22]=2[CH:21]=[CH:20][CH:19]=1)[C:12](OCC)=[O:13])[CH2:8][CH3:9].C(Cl)(Cl)Cl.C(O)C>C1COCC1.CO>[CH2:27]([N:10]([CH2:7][CH2:8][CH3:9])[CH:11]([CH2:17][C:18]1[C:26]2[N:25]=[CH:24][NH:23][C:22]=2[CH:21]=[CH:20][CH:19]=1)[CH2:12][OH:13])[CH2:28][CH3:29]Lithium aluminum hydride (250 mg, 6.6 mmol) was added at 0° C. to a stirred solution of ethyl α-(dipropylamino)-1H-benzimidazole-4-propanoate (1.5 g, 4.7 mmol) in dry THF (50 mL), and the solution was allowed to warm to room temperature. TLC in 10% methanol:chloroform showed that the reaction was complete in 15 minutes. Ethanol (5 mL) was added and the solvents were removed under reduced pressure. The residue was partitioned between ethyl acetate and water. Evaporation of the ethyl acetate gave 1.3 g of β-(dipropylamino)-1H-benzimidazole-4-propanol which was used without further purification.
Loading…
