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

HRID 1410088

Reaktionsgleichung

Reaktionsgleichung von HRID 1410088
[OH-].[K+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.Br[CH2:15][C:16]([CH2:21]Br)([CH2:19]Br)[CH2:17][OH:18]>C(O)C>[C:4]1([CH3:3])[CH:5]=[CH:6][C:7]([S:10]([N:13]2[CH2:21][C:16]3([CH2:19][O:18][CH2:17]3)[CH2:15]2)(=[O:12])=[O:11])=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 6269P-ToluenesulfonamideHCID 14797Potassium HydroxideHCID 15206Pentaerythritol tribromide

Produkt 1

HCID 233198916-Tosyl-2-oxa-6-azaspiro[3.3]heptaneAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of KOH (4.98 g, 0.089 mol) and 4-methylbenzenesulfonamide (5.7 g, 0.033 mol) in 90 ml of ethanol, 3-bromo-2,2-bis(bromomethyl)propan-1-ol (9 g, 0.0277 mol) was added at room temperature and the reaction mixture was heated to reflux for 45 h. The solvent was removed by evaporation, 75 ml of 1 M KOH were added and the white suspension was left to stir for another 2 h at room temperature. The mixture was filtered and the white filter cake was rinsed with water until the washing water was neutral. The filter cake was dried under high vacuum to give 4.87 g 6-toluene-4-sulfonyl-2-oxa-6-azaspiro[3.3]heptane (69%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.70-7.68 (m, 2H), 7.36-7.34 (m, 2H), 4.58 (s, 4H), 3.90 (s, 4H), 2.45 (s, 3H).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 45 h
  3. customThe solvent was removed by evaporation, 75 ml of 1 M KOH
  4. additionwere added
  5. waitthe white suspension was left
  6. filtrationThe mixture was filtered
  7. washthe white filter cake was rinsed with water until the washing water
  8. customThe filter cake was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-18ab945b6bf84d1985df8941b90708f1
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921383B2

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