Trifluoroacetic acid → HCID 57803053, compound

HRID 2102688Notes

Reaction equation

HRID 2102688 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)(O)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 57803068HCID 57803068, compound

Product 1

HCID 57803053HCID 57803053, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of rac-6-chloro-3-cyclohexyl-3-hydroxy-1,3-dihydro-indol-2-one (0.14 g, 0.52 mmol) (from Example 19a supra) in a mixture of triethylsilane (0.25 mL, 1.58 mmol) (Aldrich) and trifluoroacetic acid (0.77 g, 7.6 mmol) (Aldrich) was heated in a 90° C. bath for 48 hours. After cooling to room temperature, mixture was diluted with ethyl acetate. Solid potassium carbonate was added and mixture stirred at room temperature for 1 hour. Mixture was filtered and concentrated. Residue was redissolved in ethyl acetate and washed with water and brine, dried (Na2SO4), filtered and concentrated. Residue was recrystallized from dichloromethane-hexanes to give rac-6-chloro-3-cyclohexyl-1,3-dihydro-indol-2-one as a grey solid. (Yield 0.11 g, 84%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationMixture was filtered
  3. concentrationconcentrated
  4. dissolutionResidue was redissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customResidue was recrystallized from dichloromethane-hexanes

Sources & evidence

ORD record
ord-66b8df66b7d844b39cc4cd9d1742a377
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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