Sodium Hydroxide → HCID 86600895, compound

HRID 2110333Notes

Reaction equation

HRID 2110333 reaction equation
[N:1]1([CH:10]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:11](OS(C)(=O)=O)[CH2:12]OC(=O)C2C=CC([N+]([O-])=O)=CC=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-:36].[Na+]>O1CCOCC1.O>[O:36]1[CH2:12][CH:11]1[CH:10]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86600894HCID 86600894, compound

Product 1

HCID 86600895HCID 86600895, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (2RS,3RS)-4-nitro-benzoic acid-3-indol-1-yl-2-methanesulfonyloxy-3-phenyl-propyl ester in dioxane (30 mL) and a 2N aqueous solution of sodium hydroxide (15 mL) were stirred at room temperature for 4 hours. The mixture was diluted with water and extracted with ethyl acetate. The extract was washed with 5% aqueous sodium carbonate and water, dried over anhydrous sodium sulfate, filtered, and concentrated to give (1RS,2SR)-1-(oxiranyl-phenyl-methyl)-1H-indole as an oil. MS (ESI) m/z 250 ([M+H]+).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 5% aqueous sodium carbonate and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-668c9d67f30740bebd5665786357df12
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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