Sodium borohydride → HCID 67220195, compound
Reaction equation
[OH:1][C:2]1[C:7]2[N:8]([CH2:12][CH2:13][O:14][CH3:15])[C:9]([CH3:11])=[N:10][C:6]=2[CH:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[C:3]=1[CH2:20][CH2:21][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[BH4-].[Na+]>C(O)C>[OH:1][C:2]1[C:7]2[N:8]([CH2:12][CH2:13][O:14][CH3:15])[C:9]([CH3:11])=[N:10][C:6]=2[CH:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[C:3]=1[CH2:20][CH2:21][CH:22]([OH:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of methyl 7-hydroxy-1-(2-methoxyethyl)-2-methyl-6-(3-oxo-3-phenylpropyl)-1H-benzimidazole-5-carboxylate (2.08 g, 5.25 mmol, Step 9) in ethanol (50 mL) was added sodium borohydride (298 mg, 7.87 mmol) at room temperature. After stirring at the same temperature for 4 hours, the solvent was evaporated, and the residue was poured onto saturated sodium hydrogencarbonate aqueous solution, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane/methanol (20:1) to afford the title compound as a brown amorphous (2.08 g, 99%).