Potassium sodium tartarate → HCID 11043960, compound

HRID 1457321Notes

Reaction equation

HRID 1457321 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[O:13])[CH:7]([CH2:14][C:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=O)[CH2:6][CH2:5]2.[H-].COCCO[Al+]OCCOC.[Na+].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[CH:8]([OH:13])[CH:7]([CH2:14][CH2:15][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 22104505HCID 22104505, compound

Product 1

HCID 11043960HCID 11043960, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 1-[(1,2,3,4-tetrahydro-6,7-dimethyl-1-oxo-2-naphthalenyl)acetyl]pyrrolidine (9.5 g) in toluene (100 ml) was added dropwise with stirring a 70% solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene (29.0 g) under ice-cooling, and the mixture was stirred at the same temperature for one hour, and stirred at 25° C. for three hours. The reaction mixture was cooled again with ice, and thereto was added dropwise a saturated aqueous sodium potassium tartrate solution (30 ml), and the mixture was stirred at the same temperature for 30 minutes in order to decompose the excess amount of the reducing agent. The organic layer was separated, washed successively with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate=10:1), and the fractions containing the desired compound were combined, and concentrated under reduced pressure to give the desired compound (8.5 g) as an oily product.

Workup

  1. temperaturecooling
  2. stirringstirred at 25° C. for three hours
  3. temperatureThe reaction mixture was cooled again with ice
  4. stirringthe mixture was stirred at the same temperature for 30 minutes in order
  5. customThe organic layer was separated
  6. washwashed successively with water
  7. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto remove the solvent
  10. customThe residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate=10:1)
  11. additionthe fractions containing the desired compound
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44aa683b7bc64358bed800d7e37edeff
Source dataset
uspto-grants-1998_12
Patent number
US05847159

Reaction notes

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