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

HRID 38212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 38212
[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-b39c67d725c74f58ab23fc80867460fd
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524724B2

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