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

HRID 581815Notes

Reaction equation

HRID 581815 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 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).

Workup

  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)

Sources & evidence

ORD record
ord-47738f2be4c548f380cc2d23b2c9e58b
Source dataset
uspto-grants-1999_07
Patent number
US05922723

Reaction notes

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