(RS)-S-(4-nitrophenyl)-N-(2-methoxy-acetyl)-S-methylsulfoximide → (RS)-S-(4-aminophenyl)-N-(2-methoxy-acetyl)-S-methylsulphoximide

HRID 38211Notes

Reaction equation

HRID 38211 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:18])(=[N:12][C:13](=[O:17])[CH2:14][O:15][CH3:16])=[O:11])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:18])(=[N:12][C:13](=[O:17])[CH2:14][O:15][CH3:16])=[O:11])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 59550858(RS)-S-(4-nitrophenyl)-N-(2-methoxy-acetyl)-S-methylsulfoximide

Product 1

HCID 59550852(RS)-S-(4-aminophenyl)-N-(2-methoxy-acetyl)-S-methylsulphoximideYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

107 mg (0.39 mmol) (RS)—S-(4-nitrophenyl)-N-(2-methoxy-acetyl)-S-methylsulfoximide is dissolved in 13.6 ml ethanol and treated with 40 mg palladium on activated charcoal (10% Pd). The mixture is stirred under hydrogen at normal pressure for 60 minutes at 24 C. The catalyst is filtered off and the solution concentrated. After chromatographic purification (silica gel, hexane/ethyl acetate (0-50% ethyl acetate)), 50 mg (53%) of the desired product is obtained.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe solution concentrated
  3. customAfter chromatographic purification (silica gel, hexane/ethyl acetate (0-50% ethyl acetate))

Sources & evidence

ORD record
ord-0823e370808c45eb8b1d687f7f7759e9
Source dataset
uspto-grants-2013_09
Patent number
US08524724B2

Reaction notes

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