Water → HCID 15411702, compound

Reaction equation

[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11](=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]=2[N:4]=[C:3]1[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH4-].[Na+].O>CO>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]([OH:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]=2[N:4]=[C:3]1[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Procedure

To a suspension of ethyl 3-(1-methyl-2-(2-phenylethyl)benzimidazol-4-yl)-3-oxopropanoate (0.80 g) obtained in Inventive Example 10 in anhydrous methanol (16 mL), was added sodium borohydride in small portions which was cooled in an ice bath. After stirring for 20 minutes at room temperature, the reaction solution was poured into water and concentrated under a reduced pressure. The thus obtained residue was extracted with ethyl acetate, and the organic layer was washed with water and brine in that order. The organic layer was dried over anhydrous sodium sulfate and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain the title compound as white crystal (0.39 g).