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

HRID 238143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238143
[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

Komponenten

3

Edukt 1

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

Produkt 1

HCID 59550833(RS)-S-(4-aminophenyl)-N-(2-methoxy-ethyl)-S-methylsulfoximideAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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))

Quellen und Nachweise

ORD-Eintrag
ord-38111730cf5f4fdf98e9ea3a58a436f1
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642611B2

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