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

HRID 1080676Notes

Reaction equation

HRID 1080676 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

HCID 53673921HCID 53673921, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 23938PalladiumSolvent

Procedure

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 filteration 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).

Workup

  1. customThe catalyst was removed by filteration 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)

Sources & evidence

ORD record
ord-8c8e0d369f6040a1a21206117f78eab2
Source dataset
uspto-grants-1996_12
Patent number
US05583140

Reaction notes

Loading…