(Trifluoromethyl)trimethylsilane → (R)-2-Methyl-propane-2-sulfinic acid [(S)-1-(4-chloro-3,5-dimethyl-phenyl)-2,2,2-trifluoro-ethyl]-amide

HRID 1629736Notes

Reaction equation

HRID 1629736 reaction equation
[Si]([C:5]([F:8])([F:7])[F:6])(C)(C)C.[Cl:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13](/[CH:17]=[N:18]/[S@@:19]([C:21]([CH3:24])([CH3:23])[CH3:22])=[O:20])=[CH:12][C:11]=1[CH3:25]>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.C1C=CC([Si-](F)(F)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:9][C:10]1[C:11]([CH3:25])=[CH:12][C:13]([C@H:17]([NH:18][S@@:19]([C:21]([CH3:23])([CH3:22])[CH3:24])=[O:20])[C:5]([F:8])([F:7])[F:6])=[CH:14][C:15]=1[CH3:16]

Participants

5

Reactant 2

HCID 552549(Trifluoromethyl)trimethylsilane2×HCID 87365021(NE,R)-N-[(4-chloro-3,5-dimethylphenyl)methylidene]-2-methylpropane-2-sulfinamide

Product 1

HCID 67345793(R)-2-Methyl-propane-2-sulfinic acid [(S)-1-(4-chloro-3,5-dimethyl-phenyl)-2,2,2-trifluoro-ethyl]-amide

Reagents, catalysts & solvents 2

HCID 9893474Tetrabutylammonium DifluorotriphenylsilicateCatalyst2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of TMS-CF3 (0.737 mL, 4.99 mmol) in THF (15 mL) was added to a solution of TBAT (2.469 g, 4.57 mmol) and INT 36 (1.13 g, 4.16 mmol) in THF (60.0 mL) at −65° C. Stirring was continued for 3 hours. Another portion of TBAT (200 mg, 0.37 mmol) was added. After 2 more hours, more TMS-CF3 (0.369 ml, 2.50 mmol) was added. The suspension became a clear solution which was quenched with saturated ammonium chloride solution, diluted with EtOAc and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude was purified by chromatography on silica gel (cyclohexane/EtOAc).

Workup

  1. customwas quenched with saturated ammonium chloride solution
  2. additiondiluted with EtOAc
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified by chromatography on silica gel (cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-0742b6a943e7425d967682b024019761
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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