Diethyl Ether → HCID 18670585, compound

HRID 1059286Notes

Reaction equation

HRID 1059286 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][N:8]1[CH2:15][CH:14]2[C:16](=O)[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9]1.CCOCC>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:7][N:8]1[CH2:15][CH:14]2[C:16](=[CH2:1])[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH2:9]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 5414983-Methyl-3-azabicyclo[3.3.1]nonan-9-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 18670585HCID 18670585, compoundYield 104.7%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 6.9 g of methyltriphenyl phosphonium bromide in toluene (30 ml) was added 2.2 g of potassium tert-butoxide at 0° C. and the resulting mixture was stirred for 30 minutes. Next, 3.0 g of 3-methyl-3-azabicyclo[3.3.1]nonan-9-one was added thereto and the mixture was reacted for 1 hour. After adding ether, the reaction mixture was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After filtering and concentrating, the residue was purified by silica gel column chromatography (eluted with ether/n-hexane) to thereby give 3.1 g of the title compound as a yellow oily substance.

Workup

  1. customthe mixture was reacted for 1 hour
  2. washthe reaction mixture was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtering
  5. concentrationconcentrating
  6. customthe residue was purified by silica gel column chromatography (eluted with ether/n-hexane)

Sources & evidence

ORD record
ord-c380773cb2894b709aa8aeababa6fd25
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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