2-Methoxyphenyl-4-[3-(cyclohexanecarbonyl)-3-(phenyl)propyl]piperazine → 1-(2-Methoxyphenyl)-4-[4-(cyclohexyl)-4-(hydroxy)-3-(phenyl)butyl]piperazine

Participants

Reaction Conditions

Reaction Steps

Into a solution of 1.21 g of Compound 5d in 60 ml of dichloromethane at −78° C., was dropped 11.5 ml of 1 M solution of diisobutylaluminum hydride (DIBAL-H) in toluene. The mixture was stirred at −78° C. for 1 h, quenched at 40° C. with a saturated aqueous solution of NH4Cl and extracted with chloroform. The collected organic layers were washed with water, dried (Na2SO4) and the solvent was evaporated under vacuum. The crude was purified by flash chromatography eluting with petroleum ether-EtOAc-2 N ammonia in methanol 30:70:2 to give 1.06 g (80%) of the title compound.

Provenance & Evidence