(Trifluoromethyl)trimethylsilane → HCID 57979769, compound

HRID 1868099Notes

Reaction equation

HRID 1868099 reaction equation
[CH3:1][C@@H:2]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])[CH2:5][CH2:4][N:3]1[S:18]([C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19].[Si]([C:34]([F:37])([F:36])[F:35])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C([O-])(O)=O.[Na+]>[F:35][C:34]([F:37])([F:36])[C:27]([C:24]1[CH:23]=[CH:22][C:21]([S:18]([N:3]2[CH2:4][CH2:5][N:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:14]([F:16])([F:17])[F:15])[CH2:7][C@H:2]2[CH3:1])(=[O:20])=[O:19])=[CH:26][CH:25]=1)([OH:29])[CH3:28]

Participants

6

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 68549254HCID 68549254, compound

Product 1

HCID 57979769HCID 57979769, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a 50 mL flask containing (R)-1-{4-[2-methyl-4-(2-trifluoromethyl-phenyl)-piperazine-1-sulfonyl]-phenyl}-ethanone (200 mg, 0.47 mmol) and 2.34 mL of 0.5 M TMS-CF3, was added 0.47 mL of 1.0 M tetrabutylammonium fluoride in THF at 0° C. After stirring for 4 h, the solution was diluted with saturated NaHCO3, extracted (2×CH2Cl2), washed with brine and dried over Na2SO4, and concentrated under reduced pressure. Purification by flash column chromatography to yield 1,1,1-trifluoro-2-[4-({(2R)-2-methyl-4-[2-(trifluoromethyl)phenyl]piperazin-1-yl}sulfonyl)phenyl]propan-2-ol in 31.8% yield (74.1 mg) as a colorless oil.

Workup

  1. extractionextracted (2×CH2Cl2)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-eade72f752db4d7bb2a10dba950e72af
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

Loading…