Dimethylformamide → HCID 117913965, compound

HRID 522260Notes

Reaction equation

HRID 522260 reaction equation
[H-].[Na+].[CH2:3]1[CH2:7][O:6][CH2:5][CH2:4]1.[CH2:8]([N:15]1[CH2:21][CH:20]2[C:22](=O)[CH:17]([CH2:18][CH2:19]2)[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CN(C=[O:28])C>CCOC(C)=O.O>[CH2:7]([O:6][C:5](=[O:28])[CH:4]=[C:22]1[CH:17]2[CH2:18][CH2:19][CH:20]1[CH2:21][N:15]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:16]2)[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 156391343-Benzyl-3-azabicyclo(3.2.1)octan-8-one

Product 1

HCID 117913965HCID 117913965, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

60% sodium hydride (109 mg) was added to a mixture of triethyl phosphonoacetate (1.02 g) and THF (12 mL) at 0° C. in a nitrogen atmosphere, and the mixture was stirred at room temperature for 10 minutes. 3-Benzyl-3-azabicyclo[3.2.1]octan-8-one (978 mg) and DMF (5 mL) were added to the mixture, and the mixture was stirred at room temperature overnight. After water was added to the reaction mixture, extraction thereof was performed using EtOAc, and the extract was washed with saturated brine. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=97:3 to 80:20), whereby ethyl(3-benzyl-3-azabicyclo[3.2.1]oct-8-ylidene)acetate (362 mg) was obtained as a colorless liquid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. washthe extract was washed with saturated brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=97:3 to 80:20)

Sources & evidence

ORD record
ord-8d621d2df33340ee93e2963a78559f42
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

Loading…