Lithium aluminum hydride → (2-Amino-1-cyclohexyl-1H-benzimidazol-5-yl)methanol

Participants

Reaction Steps

In a 20 mL vial, ethyl 2-amino-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate (101.5 mg, 0.0003532 mol) was dissoled in tetrahydrofuran (2 mL, 0.02 mol). While stirring under nitrogen, a solution of 1.0 M of lithium tetrahydroaluminate in tetrahydrofuran (1.0 mL) was added dropwise via a syringe to the reaction mixture. An initial reddish color occured followed by the reaction mixture becoming straw colored and a precipitate formed. After 1 hour the reaction was quenched by the dropwise addition of saturated ammonium chloride (1 mL). The mixture was extracted with ethyl acetate three times, the combined organic phases dried over sodium sulfate and concentrated to give the title compound (79.4 mg) as an off white solid.

Provenance & Evidence