P-Toluenesulfonamide → 6-Tosyl-2-oxa-6-azaspiro[3.3]heptane

HRID 1850313Notes

Reaction equation

HRID 1850313 reaction equation
Br[CH2:2][C:3]([CH2:8]Br)([CH2:6]Br)[CH2:4][OH:5].[OH-].[K+].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1>CCO>[C:12]1([CH3:22])[CH:13]=[CH:14][C:15]([S:18]([N:21]2[CH2:8][C:3]3([CH2:6][O:5][CH2:4]3)[CH2:2]2)(=[O:19])=[O:20])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 14797Potassium HydroxideHCID 15206Pentaerythritol tribromide

Product 1

HCID 233198916-Tosyl-2-oxa-6-azaspiro[3.3]heptaneYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-bromo-2,2-bis(bromomethyl)propanol (127) (3.25 g, 10 mmol) and potassium hydroxide (1.12 g, 20 mmol, in 10 mL water) in EtOH (20 mL) were added toluene-4-sulfonamide (3.76 g, 22 mmol). The reaction mixture was refluxed for 2 h, evaporated to remove EtOH then diluted with EAOAc (20 mL), washed with H2O (20 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4, and filtered, evaporated to give the product to give 6-(toluene-4-sulfonyl)-2-oxa-6-aza-spiro[3.3]heptane (128) (1.6 g, 6.3 mmol, yield: 63%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customevaporated
  3. customto remove EtOH
  4. additionthen diluted with EAOAc (20 mL)
  5. washwashed with H2O (20 mL)
  6. washThe organic layer was washed with brine (20 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customto give the product

Sources & evidence

ORD record
ord-9a27ba83252e4f7291dd076301e982ea
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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