Formaldehyde → HCID 19097385, compound

HRID 2255409Notes

Reaction equation

HRID 2255409 reaction equation
Cl.[CH3:2][CH:3]1[C:8]2([CH3:12])[C:9]([CH3:11])=[CH:10][CH:5]([CH:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7]2)[N:4]1[CH2:18]C1C=CC=CC=1.C(N(CC)CC)C.C=O>[Pd].C(O)C>[CH3:18][N:4]1[CH:3]([CH3:2])[C:8]2([CH3:12])[CH:9]([CH3:11])[CH2:10][CH:5]1[CH:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7]2

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 8471TriethylamineHCID 19097417HCID 19097417, compound

Product 1

HCID 19097385HCID 19097385, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl 3,4,8-trimethyl-2-(phenylmethyl)-2-azabicyclo[2.2.2]-oct-7-ene-6-carboxylate hydrochloride (17.4 g, 49.7 mol), 10% palladium on carbon (1.7 g) and ethanol (200 mL) was hydrogenated on a Parr hydrogenator at 50 psi for 6 hours. The mixture was removed from the Parr hydrogenator, cooled to 0° C. and triethylamine (7.0 mL, 50 mmol), followed by 37% formaldehyde (4.1 mL, 55 mmol) were added. The mixture was then placed back on the Parr hydrogenator at 50 psi for 1 hour. The reaction mixture was removed from the Parr hydrogenator, the catalyst was removed by filtration and the solvent was removed in vacuo. The residue was dissolved in water, basified with concentrated ammonium hydroxide (20 mL) and extracted with ether (3×300 mL). The combined organic layers were washed with brine (50 mL), dried over potassium carbonate and concentrated in vacuo to afford 11.5 g (96%) of ethyl 2,3,4,8-tetramethyl-2-azabicyclo[2,2,2]-octane-6-carboxylate as a pale yellow oil.

Workup

  1. customThe mixture was removed from the Parr hydrogenator
  2. additionwere added
  3. waitThe mixture was then placed back on the Parr hydrogenator at 50 psi for 1 hour
  4. customThe reaction mixture was removed from the Parr hydrogenator
  5. customthe catalyst was removed by filtration
  6. customthe solvent was removed in vacuo
  7. dissolutionThe residue was dissolved in water
  8. extractionextracted with ether (3×300 mL)
  9. washThe combined organic layers were washed with brine (50 mL)
  10. dry with materialdried over potassium carbonate
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec4e1842a2964372bcf7d61287fe926c
Source dataset
uspto-grants-1993_08
Patent number
US05240935

Reaction notes

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