1,1'-Carbonyldiimidazole → 3,4-Dimethoxyphenethyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

HRID 1596464

Reaktionsgleichung

Reaktionsgleichung von HRID 1596464
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][CH2:7][OH:8].[C:14]([N:21]1[CH:25]=[CH:24]N=[CH:22]1)(N1C=CN=C1)=[O:15].[CH2:26]([N:33]1[CH2:40]C2C[CH:35]([CH2:36]NC2)[CH2:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[CH2:26]([N:33]1[CH2:34][CH:35]2[CH2:36][CH:24]([CH2:25][N:21]([C:14]([O:8][CH2:7][CH2:6][C:5]3[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:15])[CH2:22]2)[CH2:40]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 819113,4-Dimethoxyphenethyl alcoholHCID 130594823-Benzyl-3,7-diazabicyclo[3.3.1]nonane

Produkt 1

HCID 217019373,4-Dimethoxyphenethyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylateAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3,4-Dimethoxyphenethyl alcohol (3.64 g; 20 mmol) was added to a stirred suspension of 1,1′-carbonyldiimidazole (3.24 g; 20 mmol) in THF (20 mL), and the mixture was refluxed for 12 h. A solution of 3-benzyl-3,7-diazabicyclo[3.3.1]nonane (4.33 g; 20 mmol; see Example E above) in THF (20 mL) was added and the reaction mixture was refluxed overnight. The solvent was removed and the residue dissolved in H2SO4 (2M; 25 mL) and extracted with diethyl ether. NaOH (3.5 mL; 5M) was added and the aqueous phase extracted with DCM. The organic layer was separated, dried and subjected to column chromatography (DCM:MeOH; gradient 0 to 30% MeOH) to give the sub-title compound in a 29% yield.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 12 h
  2. temperaturethe reaction mixture was refluxed overnight
  3. customThe solvent was removed
  4. dissolutionthe residue dissolved in H2SO4 (2M; 25 mL)
  5. extractionextracted with diethyl ether
  6. additionNaOH (3.5 mL; 5M) was added
  7. extractionthe aqueous phase extracted with DCM
  8. customThe organic layer was separated
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-21b65b4160884ee58a89a1737c265300
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06291475B1

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