Acetic Acid → HCID 19883424, compound

HRID 846594Notes

Reaction equation

HRID 846594 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[CH2:2]2.[N+:10]([CH3:13])([O-:12])=[O:11].[O-]CC.[Na+].C(O)C.C(O)(=O)C>C(O)C>[N+:10]([CH2:13][C:3]1([OH:9])[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 195073-QuinuclidinoneHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 19883424HCID 19883424, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 3-quinuclidinone (24.4 g, 0.195 mole) and nitromethane (15.9 g, 0.260 mole) in absolute ethanol (100 ml) was added to a cooled (0° C.) mechanically stirred solution of 21% sodium ethoxide/ethanol (64.8 g, 200 mole) in absolute ethanol (300 ml) under nitrogen. The mixture was stirred at room temperature for one hour, then at 55°(±5°) C. for 18 hours. The cooled suspension was treated dropwise with acetic acid (13.2 g, 0.220 mole), filtered through Celite®, washed with methanol, and concentrated in vacuo. The residue was filtered through alumina (eluted with 1:2 methylene chloride/methanol), concentrated in vacuo, and triturated from acetonitrile to afford 8.44 g (23%) of the title compound as an off-white solid.

Workup

  1. additionwas added to
  2. customat 55°
  3. custom(±5°) C
  4. waitfor 18 hours
  5. filtrationfiltered through Celite®
  6. washwashed with methanol
  7. concentrationconcentrated in vacuo
  8. filtrationThe residue was filtered through alumina (eluted with 1:2 methylene chloride/methanol)
  9. concentrationconcentrated in vacuo
  10. customtriturated from acetonitrile

Sources & evidence

ORD record
ord-0b7bbab60ff8433c9fa3b66228744c84
Source dataset
uspto-grants-1992_08
Patent number
US05137895

Reaction notes

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