Hydrogen Peroxide → HCID 9858213, compound

HRID 1581724Notes

Reaction equation

HRID 1581724 reaction equation
[CH2:1]([O:4][C:5](=[O:22])[NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])[CH:2]=[CH2:3].B.C1C[O:27]CC1.[OH-].[Na+].OO>C1COCC1>[OH:27][CH2:3][CH2:2][CH2:1][O:4][C:5](=[O:22])[NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 9922403HCID 9922403, compound

Product 1

HCID 9858213HCID 9858213, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[3-(2-Acetylamino-ethyl)-1H-indol-5-yl]-carbamic acid allyl ester (1 mmol) is dissolved in THF (27 mL) and borane-THF (2 mmol) added dropwise. After 2 h, sodium hydroxide (4 mL of 3 M) and hydrogen peroxide (4 mL of 30%) are added and the solution stirred an additional 1 h. The solution is concentrated to half its volume, 10 mL water is added and it is extracted with ethyl acetate (4×25 mL). The combined extracts are washed with brine, dried, the solvent removed in vacuo, and the product chromatographed on silica gel with 5% methanol in chloroform as eluent.

Workup

  1. concentrationThe solution is concentrated to half its volume, 10 mL water
  2. additionis added
  3. extractionit is extracted with ethyl acetate (4×25 mL)
  4. washThe combined extracts are washed with brine
  5. customdried
  6. customthe solvent removed in vacuo
  7. customthe product chromatographed on silica gel with 5% methanol in chloroform as eluent

Sources & evidence

ORD record
ord-89091b664dbe45739a3597c658b55185
Source dataset
uspto-grants-2004_05
Patent number
US06730707B2

Reaction notes

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