Methyl trifluoromethyl ketone → HCID 56932985, compound

HRID 1972370Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Li]CCCC.[F:28][C:29]([F:34])([F:33])[C:30](=[O:32])[CH3:31]>C1COCC1>[F:28][C:29]([F:34])([F:33])[C:30]([C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)([OH:32])[CH3:31]

Participants

Conditions

Temperature: -78 °C

Procedure

A 250 ml, round-bottomed flask was charged with 1-(4-bromophenyl)-4-(phenylsulfonyl)piperazine (0.50 g, 1.31 mmol) and 20 mL of THF. After cooling to −78° C., n-BuLi (0.603 mL, 2.5 M in hexanes, 1.51 mmol) was slowly added. The mixture was stirred at −78° C. for 30 min, then 1,1,1-trifluoro-2-propanone (0.441 g, 3.93 mmol, Sigma-Aldrich, St. Louis, Mo.) was added. The reaction was stirred at −78° C. for 1 h, and then quenched with saturated aqueous NH4Cl (15 mL). The organics were extracted with EtOAc (2×50 mL), dried (MgSO4), and concentrated to give an oil. Purification via column chromatography (40 g of silica, 0 to 40% EtOAc in hexanes) produced 1,1,1-trifluoro-2-(4-(4-(phenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (0.215 g) as a mixture of two enantiomers.

Workup

stirringThe reaction was stirred at −78° C. for 1 h
customquenched with saturated aqueous NH4Cl (15 mL)
extractionThe organics were extracted with EtOAc (2×50 mL)
dry with materialdried (MgSO4)
concentrationconcentrated
customto give an oil
customPurification via column chromatography (40 g of silica, 0 to 40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-235a7d351c0d4a7d93b00724d38c0620
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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