2,2,2-Trifluoro-1-(4-(4-(phenylsulfonyl)-1-piperazinyl)phenyl)ethanone → 1-Cyclopropyl-2,2,2-trifluoro-1-(4-(4-(phenylsulfonyl)-1-piperazinyl)phenyl)ethanol

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottom flask was charged with 2,2,2-trifluoro-1-(4-(4-(phenylsulfonyl)-1-piperazinyl)phenyl)ethanone (0.50 g, 1.26 mmol) and 10 mL of THF. After cooling to 0° C., cyclopropylmagnesium bromide (5.02 mL, 0.5 M in THF, 2.51 mmol, Sigma-Aldrich, St. Louis, Mo.) was added. After 10 min, the mixture was quenched with saturated aqueous NH4Cl (15 mL), extracted with EtOAc (2×50 mL), dried (MgSO4), and concentrated to give an oil. This oil was purified via column chromatography (40 g of silica, 0 to 40% EtOAc in hexanes) to give 1-cyclopropyl-2,2,2-trifluoro-1-(4-(4-(phenylsulfonyl)-1-piperazinyl)phenyl)ethanol (0.375 g) as a mixture of two enantiomers.

Provenance & Evidence