Aluminium lithium hydride → HCID 20813981, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-4-carboxylic acid methyl ester (2.36 g, 5.44 mmol) in THF (33 mL) was slowly added 1M LiAlH4 in THF (5.46 mL, 5.46 mmol) under nitrogen. The mixture turned bright yellow and was stirred for 10 min at the same temperature. The mixture was quenched with satd. Na/K tartrate (15 mL) and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine and dried with MgSO4. The residue after concentration was purified by flash chromatography (eluent dichloromethane: acetone 4:1, 3:1, 5:2, 2:1) to give 1-[4-Hydroxymethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one (1.21 g, 55%) as a white foam:

Provenance & Evidence