3-(3-Pyridyl)-2-carboethoxy-2-azabicyclo[2.2.2]oct-5-ene → HCID 53673921, Verbindung

HRID 1870794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1870794
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH:12]3[CH2:13][CH2:14][CH:9]([CH:10]=[CH:11]3)[N:8]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:2]=1>C(O)(=O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH:12]3[CH2:11][CH2:10][CH:9]([CH2:14][CH2:13]3)[N:8]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:2]=1

Komponenten

4

Edukt 1

HCID 186942083-(3-Pyridyl)-2-carboethoxy-2-azabicyclo[2.2.2]oct-5-ene

Produkt 1

HCID 53673921HCID 53673921, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 23938PalladiumLösungsmittel

Versuchsvorschrift

A solution of the (+/-)-endo and (+/-)-exo isomers of 3-(3-pyridyl)-2-carboethoxy-2-azabicyclo[2.2.2]oct-5-ene, compound (II), (750 mg, 2.90 mmol) in glacial acetic acid (0.5 mL) and Pd/C (10%) was shaken under a H2 atmosphere in a Parr apparatus for 2 hours. The catalyst was removed by filtration over a bed of Celite and the filtrate was basified by addition of a solution of 40% of NaOH in water. The aqueous basic solution was extracted with dichloromethane (4×20 mL) to give 740 mg (98%) of compound (XII). 1H NMR (CDCl3): δ 8.48 (m, 2H), 7.60 (m, 2H), 4.78 and 4.67 (m, 1H), 4.30 (m, 1H), 4.13 and 4.10 (q, 2H), 2.19 (m, 2H), 1.90 (m, 3H), 1.63 (m, 4H), 1.28 and 0.90 (t, 3H).

Aufarbeitung

  1. customThe catalyst was removed by filtration over a bed of Celite
  2. additionthe filtrate was basified by addition of a solution of 40% of NaOH in water
  3. extractionThe aqueous basic solution was extracted with dichloromethane (4×20 mL)

Quellen und Nachweise

ORD-Eintrag
ord-201c2c749555486e90a57cb85f86826b
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06100269

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