Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylate → 1-Azabicyclo[2.2.2]oct-4-yl{bis[4-(methyloxy)phenyl]}methanol

HRID 1782477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1782477
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.[N:11]12[CH2:18][CH2:17][C:14]([C:19]([O:21]CC)=O)([CH2:15][CH2:16]1)[CH2:13][CH2:12]2>C1COCC1>[N:11]12[CH2:12][CH2:13][C:14]([C:19]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[OH:21])([CH2:15][CH2:16]1)[CH2:17][CH2:18]2

Komponenten

4

Edukt 2

HCID 573424Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylateHCID 178491912HCID 178491912, Verbindung

Produkt 1

HCID 689616381-Azabicyclo[2.2.2]oct-4-yl{bis[4-(methyloxy)phenyl]}methanolAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-(methyloxy)phenylmagnesiumbromide (0.5 M in THF, 6.5 mL, 3.25 mmol) was chilled down to 0° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.1587 g, 0.866 mmol) in THF (4 mL) was slowly added to the reaction mixture at 0° C. over 20 min. The reaction was allowed to warm up to room temperature and then heated at 60° C. for 16 h. The reaction was chilled in an ice bath, quenched with saturated NH4Cl, and concentrated under vacuum. The resulting residue was treated with H2O and extracted with EtOAc. The combined organic layers were dried with MgSO4, filtered, and concentrated under vacuum to yield the desired product (0.273 g, 89.0%). EI-MS m/z 354(M+H+) Rt (1.74 min).

Aufarbeitung

  1. temperatureheated at 60° C. for 16 h
  2. temperatureThe reaction was chilled in an ice bath
  3. customquenched with saturated NH4Cl
  4. concentrationconcentrated under vacuum
  5. additionThe resulting residue was treated with H2O
  6. extractionextracted with EtOAc
  7. dry with materialThe combined organic layers were dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e746f90ebe61427490bb4048ac73cd6c
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07498440B2

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