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Methanesulfonic Acid → 3-Benzyl-7-(phenylsulfonyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane

HRID 898790
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 898790
[CH2:1]([N:8]1[CH2:15][CH:14]([OH:16])[CH2:13][N:12]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:11][CH:10](O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(O)(=O)=O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH:10]2[O:16][CH:14]([CH2:13][N:12]([S:17]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)(=[O:18])=[O:19])[CH2:11]2)[CH2:15]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 6395Methanesulfonic AcidHCID 11268889HCID 11268889, Verbindung

Produkt 1

HCID 160364063-Benzyl-7-(phenylsulfonyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonaneAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

The crude product from step (ii) above was dissolved in warm toluene (150 mL) and treated with anhydrous methanesulfonic acid (50 mL). Toluene (105 mL) was removed from the mixture by distillation at reduced pressure (28 mbar). The remaining mixture was then heated to 110° C. for 6.5 h. The mixture was allowed to cool to 30° C. and the remaining toluene removed by distillation under reduced pressure (25 mbar). The mixture was cooled in an ice/water bath to 40° C. and then treated with water (100 mL), which caused the internal temperature to rise to 70° C. After cooling to 20° C. dichloromethane (80 mL) was added. The mixture was basified by the portionwise addition of aqueous sodium hydroxide solution (10 M, 80 mL), such that the internal temperature remained below 300° C. This took 20 minutes. The dicholoromethane layer was separated and evaporated nearly to dryness in vacuo. Methanol (50 mL) was added and the solvent was again removed in vacuo. The resulting solid was suspended in MeOH (50 mL) and filtered. The filter cake was washed with methanol (20 mL) and the resulting solid dried by air suction to give the title compound as a white crystalline solid (3.46 g, 15% over 3 steps).

Aufarbeitung

  1. customToluene (105 mL) was removed from the mixture by distillation at reduced pressure (28 mbar)
  2. temperatureto cool to 30° C.
  3. customthe remaining toluene removed by distillation under reduced pressure (25 mbar)
  4. temperatureThe mixture was cooled in an ice/water bath to 40° C.
  5. additiontreated with water (100 mL), which
  6. customto rise to 70° C
  7. temperatureAfter cooling to 20° C. dichloromethane (80 mL)
  8. additionwas added
  9. additionThe mixture was basified by the portionwise addition of aqueous sodium hydroxide solution (10 M, 80 mL), such that the internal temperature
  10. customremained below 300° C
  11. customThis took 20 minutes
  12. customThe dicholoromethane layer was separated
  13. customevaporated nearly to dryness in vacuo
  14. additionMethanol (50 mL) was added
  15. customthe solvent was again removed in vacuo
  16. filtrationfiltered
  17. washThe filter cake was washed with methanol (20 mL)
  18. customthe resulting solid dried by air suction

Quellen und Nachweise

ORD-Eintrag
ord-b78e5789c02844188da583804c643c38
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07351821B2

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