Ethyl Acetate → HCID 86758843, compound

HRID 1059283Notes

Reaction equation

HRID 1059283 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6]P(OCC)(OCC)=O)=[O:5].[H-].[Na+].[CH3:17][N:18]1[CH2:25][CH:24]2[C:26](=O)[CH:20]([C@H:21]([CH3:29])[CH2:22][C@H:23]2[CH3:28])[CH2:19]1.C(OCC)(=O)C>O1CCCC1>[CH3:17][N:18]1[CH2:25][CH:24]2[C:26](=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:20]([C@H:21]([CH3:29])[CH2:22][C@H:23]2[CH3:28])[CH2:19]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 69885098HCID 69885098, compound

Product 1

HCID 86758843HCID 86758843, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 130 g of triethyl phosphono acetate in tetrahydrofuran (600 ml) was added 25 g of sodium hydride (oily: 60% or above) under ice-cooling and the resulting mixture was stirred at room temperature for 10 minutes. Then a solution of 70 g of the crude (6R*,8R*)-3,6,8-trimethyl-3-azabicyclo[3.3.1]nonan-9-one in tetrahydrofuran (300 ml) was added thereto and the reaction mixture was heated under reflux for 2 hours. After adding ethyl acetate, the reaction mixture was washed twice with a saturated aqueous solution of sodium chloride and the organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 31.5 g of the title compound as a pale yellow oily substance.

Workup

  1. temperaturecooling
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 2 hours
  4. washthe reaction mixture was washed twice with a saturated aqueous solution of sodium chloride
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-09cd051259064bf3a92c46eec36a8f29
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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