HCID 21082211, compound → HCID 11553121, compound

HRID 346830Notes

Reaction equation

HRID 346830 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([O:20][Si](CC)(CC)CC)([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])[CH:8]=2)[N:3]1[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1(C)C=CC=CC=1.O=[Mn]=O>[F:15][C:12]([F:13])([F:14])[C:11]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:2]([CH3:1])=[CH:10]2)([OH:20])[C:16]([F:19])([F:18])[F:17]

Participants

4

Reactant 1

HCID 21082211HCID 21082211, compound

Product 1

HCID 11553121HCID 11553121, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

89 mg (ca. 0.17 mmol) of the crude 2-methyl-1-phenethyl-5-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-2,3-dihydro-1H-indole obtained (example 55) were dissolved in 1 mL of toluene and treated with 92 mg (1.1 mmol) of MnO2 powder. The mixture was stirred at 80° C. for 48 hrs, filtrated and the solvent evaporated. The residue was dissolved in 1 mL of THF and treated with 0.08 mL of a 1M TBAF solution in THF. Stirring for 30 min, evaporation of the solvent and column chromagraphy on silica gel with n-heptane/EtOAc 3:1 yielded 31 mg (ca. 33%) of 1,1,1,3,3,3-hexafluoro-2-(2-methyl-1-phenethyl-1H-indol-5-yl)-propan-2-ol, light brown oil, MS: 400 (M−H)−.

Workup

  1. filtrationfiltrated
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in 1 mL of THF
  4. additiontreated with 0.08 mL of a 1M TBAF solution in THF
  5. stirringStirring for 30 min
  6. customevaporation of the solvent and column chromagraphy on silica gel with n-heptane/EtOAc 3:1

Sources & evidence

ORD record
ord-f4979d08afae4842ad2b9981e604519f
Source dataset
uspto-grants-2007_02
Patent number
US07173048B2

Reaction notes

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