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

HRID 238143Notes

Reaction equation

HRID 238143 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:16])(=[N:10][C:11](=O)[CH2:12][O:13][CH3:14])=[O:9])=[CH:4][CH:3]=1>O1CCCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH3:16])(=[N:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 59550852(RS)-S-(4-aminophenyl)-N-(2-methoxy-acetyl)-S-methylsulphoximide

Product 1

HCID 59550833(RS)-S-(4-aminophenyl)-N-(2-methoxy-ethyl)-S-methylsulfoximideYield 82.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

493 mg (2.03 mmol) (RS)—S-(4-aminophenyl)-N-(2-methoxy-acetyl)-S-methylsulphoximide is dissolved in 67.8 ml tetrahydrofuran, cooled in the ice-bath and treated dropwise with 6.13 ml (6.13 mmol) borane tetrahydrofuran complex. The mixture is stirred for 90 minutes and quenched with one drop of methanol and one drop of water. After chromatographic purification (silica gel, hexane/ethyl acetate (0-50% ethyl acetate)), 383 mg (82%) of the desired product is obtained.

Workup

  1. additiontreated dropwise with 6.13 ml (6.13 mmol) borane tetrahydrofuran complex
  2. customquenched with one drop of methanol and one drop of water
  3. customAfter chromatographic purification (silica gel, hexane/ethyl acetate (0-50% ethyl acetate))

Sources & evidence

ORD record
ord-38111730cf5f4fdf98e9ea3a58a436f1
Source dataset
uspto-grants-2014_02
Patent number
US08642611B2

Reaction notes

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