Diisobutylaluminumhydride → HCID 21471554, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the cis and trans isomers of ethyl 1-[4-(2-keto-1-benzimidazolinyl)piperidin-1-yl]cyclohexane-4-carboxylate (2.16 g) in dry toluene (150 mL) at -90° C. under argon, was added diisobutylaluminum hydride (11.6 mL of a 1.5M solution in toluene). The reaction mixture was stirred at -90° C. for 1 h, then quenched with methanol (1 mL) followed by saturated sodium potassium tartrate (50 mL). The layers were separated, the aqueous layer was extracted with 2×100 mL of ethyl acetate, and the combined organic layers were dried over MgSO4 and concentrated to dryness under reduced pressure to give the cis and trans isomers of 1-[4-(2-keto-1-benzimidazolinyl)piperidin-1-yl]cyclohexane-4-carboxaldehyde as a colorless foam (1.82 g).

Provenance & Evidence