Hydrochloric Acid → 4-Hydroxy-3,3-dimethyl-1-butanesulfonamide

HRID 274287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274287
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][S:8]([CH2:11][CH2:12][C:13]([CH3:20])([CH3:19])[C:14](OCC)=[O:15])(=[O:10])=[O:9].Cl>O1CCCC1>[OH:15][CH2:14][C:13]([CH3:20])([CH3:19])[CH2:12][CH2:11][S:8]([NH2:7])(=[O:9])=[O:10]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 10775463Ethyl 2,2-dimethyl-4-sulfamoylbutanoateHCID 21226445Aluminium lithium hydride2×

Produkt 1

HCID 107499174-Hydroxy-3,3-dimethyl-1-butanesulfonamideAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

While a suspension of 0.35 g of lithium aluminum hydride in 30 ml of tetrahydrofuran was stirred with ice-cooling, a solution of 1.5 g of ethyl 4-aminosulfonyl-2,2-dimethylbutyrate in 8 ml of tetrahydrofuran was added dropwise. After completion of dropwise addition, the mixture was stirred at 0° C. for 30 minutes and, then, at room temperature for 30 minutes. To this reaction mixture was added aqueous tetrahydrofuran for decomposition of excess lithium aluminum hydride and the mixture was neutralized with 2N-hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried (MgSO4) and the solvent was distilled off. The residue was subjected to silica gel column chromatography and elution was carried out with hexane-ethyl acetate (1:1) to provide 0.94 g of the title compound. m.p.: 75°-76° C.

Aufarbeitung

  1. temperaturecooling
  2. additionAfter completion of dropwise addition
  3. stirringthe mixture was stirred at 0° C. for 30 minutes
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationthe solvent was distilled off
  8. washThe residue was subjected to silica gel column chromatography and elution

Quellen und Nachweise

ORD-Eintrag
ord-cef947584fe1471b85f5dcdc74cab43f
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389633

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