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

HRID 274287Notes

Reaction equation

HRID 274287 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 107499174-Hydroxy-3,3-dimethyl-1-butanesulfonamideYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cef947584fe1471b85f5dcdc74cab43f
Source dataset
uspto-grants-1995_02
Patent number
US05389633

Reaction notes

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