Water → 11-Benzyl-5-difluoromethoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene

HRID 49166

Reaktionsgleichung

Reaktionsgleichung von HRID 49166
[CH2:1]([N:8]1[CH2:19][CH:18]2[CH2:20][CH:10]([CH2:11][C:12]3[CH:13]=[C:14]([OH:21])[CH:15]=[CH:16][C:17]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[CH:23](Cl)([F:25])[F:24].[OH-].[K+]>O1CCOCC1>[CH2:1]([N:8]1[CH2:19][CH:18]2[CH2:20][CH:10]([CH2:11][C:12]3[CH:13]=[C:14]([O:21][CH:23]([F:25])[F:24])[CH:15]=[CH:16][C:17]=32)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6372ChlorodifluoromethaneHCID 14797Potassium HydroxideHCID 992176211-Benzyl-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-5-ol

Produkt 1

HCID 1026838511-Benzyl-5-difluoromethoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

11-Benzyl-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-5-ol (572 mg, 2.05 mmol) was stirred in dioxane (5 mL) and H2O (1 mL) at reflux under a balloon of freon (HCF2Cl). To this was added 3N KOH dropwise so as to maintain a pH˜12. The consumption of starting material was monitored by TLC for over 2 hours. The reaction was cooled, diluted with H2O (40 mL) and extracted with EtOAc. The organic layer was washed with a sat. aq. Na2CO3 soln. (25 mL) and brine (25 mL), dried (MgSO2), filtered and concentrated to an oil (620 mg, 92%). GCMS m/e 329 (M+).

Aufarbeitung

  1. temperatureto maintain a pH˜12
  2. customThe consumption of starting material
  3. customwas monitored by TLC for over 2 hours
  4. temperatureThe reaction was cooled
  5. additiondiluted with H2O (40 mL)
  6. extractionextracted with EtOAc
  7. washThe organic layer was washed with a sat. aq. Na2CO3 soln
  8. dry with material(25 mL) and brine (25 mL), dried (MgSO2)
  9. filtrationfiltered
  10. concentrationconcentrated to an oil (620 mg, 92%)

Quellen und Nachweise

ORD-Eintrag
ord-27242166685745c097b855f63cda34c3
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706702B2

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