4-allyl-5-hydroxy-N-neopentylindole → 5-hydroxy-4-propyl-N-neopentylindole

HRID 2288892Notes

Reaction equation

HRID 2288892 reaction equation
[CH2:1]([C:4]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:2]=[CH2:3]>C(OCC)(=O)C.[Pd]>[OH:13][C:12]1[C:4]([CH2:1][CH2:2][CH3:3])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH:7]=[CH:6]2

Participants

4

Reactant 1

HCID 186724644-allyl-5-hydroxy-N-neopentylindole

Product 1

HCID 186724755-hydroxy-4-propyl-N-neopentylindole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Allyl-5-hydroxy-N-neopentylindole (Step C; 1.0 g, 3.54 mmol) was taken up in 25 mL ethyl acetate and hydrogenated (1 atm) at ambient temperature using 5% palladium on charcoal (40 mg) for 2 hours. The reaction was filtered through celite and concentrated in vacuo to provide the title compound which was used without further purification.

Workup

  1. customat ambient temperature
  2. customfor 2 hours
  3. filtrationThe reaction was filtered through celite and
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e8358747000442a9ea104bf9d9e55c1
Source dataset
uspto-grants-2000_07
Patent number
US06090839

Reaction notes

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