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

HRID 1850313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850313
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

Komponenten

5

Edukt 3

HCID 6269P-ToluenesulfonamideHCID 14797Potassium HydroxideHCID 15206Pentaerythritol tribromide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9a27ba83252e4f7291dd076301e982ea
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957073B2

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