Water → Ethyl 3-(2-Methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidineacetate

HRID 727554Notes

Reaction equation

HRID 727554 reaction equation
[CH3:1][CH:2]([CH3:24])[CH2:3][C:4]1([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]1=[O:17].I([O-])(=O)(=O)=[O:26].[Na+].O>O.[Ru](=O)=O.C(Cl)(Cl)(Cl)Cl>[CH3:1][CH:2]([CH3:24])[CH2:3][C:4]1([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:8][C:7](=[O:26])[N:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]1=[O:17]

Participants

6

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 53890699HCID 53890699, compound

Product 1

HCID 53853383Ethyl 3-(2-Methylpropyl)-2,5-dioxo-1-(2-phenylethyl)-3-pyrrolidineacetateYield 65%

Reagents, catalysts & solvents 2

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Ruthenium(IV) oxide hydrate (27 mg, 0.20 mmol) is added to a mixture of ethyl 3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (prepared similarly to that described in EXAMPLE 1, steps 1-3; 900 mg, 2.71 mmol), sodium periodate (2.71 g, 12.7 mmol), water (27 mL), and CCl4 (27 mL) at room temperature. After stirring overnight at room temperature, aqueous workup (CH2Cl2, MgSO4) and purification by column chromatography (20% EtOAc/hexane) gives 611 mg of the title compound (65%) as a colorless oil.

Workup

  1. customprepared similarly to
  2. customat room temperature
  3. customaqueous workup (CH2Cl2, MgSO4) and purification by column chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-c97d9a9927dd40a3b39ffa22aedadc1b
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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