Ethyl 2,2-dimethyl-4-sulfamoylbutanoate → 4-Hydroxy-3,3-dimethyl-1-butanesulfonamide

HRID 2395946Notes

Reaction equation

HRID 2395946 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]>O1CCCC1>[OH:15][CH2:14][C:13]([CH3:20])([CH3:19])[CH2:12][CH2:11][S:8]([NH2:7])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 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

To a suspension of 0.35 g of lithium aluminum hydride in 30 ml of tetrahydrofuran being stirred under ice cooling conditions, a solution of 1.5 g of ethyl 4-aminosulfonyl-2,2-dimethylbutyrate in 8 ml of tetrahydrofuran was added dropwise, followed by stirring at 0° C. for 30 minutes and then at room temperature (15° to 20° C.) for 30 minutes. To the reaction mixture was added aqueous tetrahydrofuran to decompose excess lithium aluminum hydride, followed by neutralization with 2 N hydrochloric acid and extraction with ethyl acetate. After the extract was washed with water and dried over MgSO4, the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with hexane:ethyl acetate (1:1) to yield 0.94 g of the title compound.

Workup

  1. stirringby stirring at 0° C. for 30 minutes
  2. extractionfollowed by neutralization with 2 N hydrochloric acid and extraction with ethyl acetate
  3. washAfter the extract was washed with water
  4. dry with materialdried over MgSO4
  5. distillationthe solvent was distilled off
  6. washeluted with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-793e992f172944d3a05f6c8aaef37d2f
Source dataset
uspto-grants-1996_02
Patent number
US05491145

Reaction notes

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