Water → (2s)-Glycidyl indol-4-yl ether

HRID 2288258Notes

Reaction equation

HRID 2288258 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[F-].[Cs+].[N+](C1C=C(S(O[CH2:26][C@H:27]2[O:29][CH2:28]2)(=O)=O)C=CC=1)([O-])=O.O>CN(C=O)C>[O:29]1[CH2:28][C@H:27]1[CH2:26][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 754211H-indol-4-olHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 10943254(2s)-Glycidyl indol-4-yl etherYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Hydroxyindole (3.0 g) was dissolved in DMF (10 ml) under nitrogen atmosphere and the solution was cooled to 0° C. Cesium fluoride (10.12 g) was added thereto and the mixture was stirred for 1 hour. Then (S)-glycidyl m-nitrobenzenesulfonate (5.84 g, 99.3% e.e.) was added thereto and the mixture was stirred for 30 hours at the same temperature. After the reaction, water was added to the mixture, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, condensed and the residue was subjected to silica gel chromatography (hexane/isopropyl alcohol; 20:1) to give 4.01 g of (S)-4-(2,3-epoxypropoxy)indole (yield 94.1%, optical purity 99.2% e.e.) as a colorless oil.

Workup

  1. stirringthe mixture was stirred for 30 hours at the same temperature
  2. additionwas added to the mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate, condensed

Sources & evidence

ORD record
ord-4012f1f38a9b4b8c97a2facaa3a64e07
Source dataset
uspto-grants-2000_07
Patent number
US06087512

Reaction notes

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