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

HRID 581815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 581815
[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 Alteration over a bed of Celite and the filterate 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 Alteration over a bed of Celite
  2. additionthe filterate 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-47738f2be4c548f380cc2d23b2c9e58b
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922723

Notizen zur Reaktion

Wird geladen…