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

HRID 1972354Notes

Reaction equation

[F:1][C:2]([F:27])([F:26])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=[O:4].[CH:28]1([Mg]Br)[CH2:30][CH2:29]1>C1COCC1>[CH:28]1([C:3]([C:5]2[CH:6]=[CH:7][C:8]([N:11]3[CH2:16][CH2:15][N:14]([S:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH2:13][CH2:12]3)=[CH:9][CH:10]=2)([OH:4])[C:2]([F:1])([F:26])[F:27])[CH2:30][CH2:29]1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

customthe mixture was quenched with saturated aqueous NH4Cl (15 mL)
extractionextracted with EtOAc (2×50 mL)
dry with materialdried (MgSO4)
concentrationconcentrated
customto give an oil
customThis oil was purified via column chromatography (40 g of silica, 0 to 40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-60ac9aee54f742808fb85d654d16c74f
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

Loading…