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

HRID 38212Notes

Reaction equation

HRID 38212 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-b39c67d725c74f58ab23fc80867460fd
Source dataset
uspto-grants-2013_09
Patent number
US08524724B2

Reaction notes

Loading…