HCID 24820425, compound → HCID 12362975, compound

HRID 1073356Notes

Reaction equation

HRID 1073356 reaction equation
O.[C:2]([C:10]([C:25]([OH:27])=[O:26])([OH:24])[C:11]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([OH:15])[C:12]([OH:14])=[O:13])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(OCC)(=O)C>[C:16]([C:11]([C:12]([OH:14])=[O:13])([OH:15])[C:10]([C:2](=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([OH:24])[C:25]([OH:27])=[O:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 24820425HCID 24820425, compound

Product 1

HCID 12362975HCID 12362975, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A resolving agent solution was obtained by adding 290 g (0.77 mol) of dibenzoyl-(-)-tartaric acid monohydrate to 1L of ethyl acetate with stirring, and the resulting solution was heated to 65°-70° C. The free amine solution of Part A was then added dropwise to the hot resolving agent solution with stirring and continued heating. After completion of the addition of the amine solution, the reaction mixture was allowed to cool to room temperature overnight with stirring to precipitate the dibenzoyl-(-)tartaric acid salt of 2-(N-propylamino)-5-methoxytetralin. The precipitated salt was collected by filtration, washed with 100 mL of acetone, dissolved in 1500 mL of hot ethyl acetate, and then reprecipitated by allowing the solution to cool overnight with stirring. The resulting crystalline salt was collected by filtration and then redissolved and reprecipitated to provide 124 g of crystalline dibenzoyl-(-)-tartaric acid salt of (-)-2-(N-propylamino)-5-methoxytetralin having a specific rotation in the range of -103° to -109°.

Workup

  1. customA resolving agent solution was obtained
  2. temperaturethe resulting solution was heated to 65°-70° C
  3. stirringwith stirring
  4. temperaturecontinued heating
  5. stirringwith stirring
  6. customto precipitate the dibenzoyl-(-)tartaric acid salt of 2-(N-propylamino)-5-methoxytetralin
  7. filtrationThe precipitated salt was collected by filtration
  8. washwashed with 100 mL of acetone
  9. dissolutiondissolved in 1500 mL of hot ethyl acetate
  10. customreprecipitated
  11. temperatureto cool overnight
  12. stirringwith stirring
  13. filtrationThe resulting crystalline salt was collected by filtration
  14. dissolutionredissolved
  15. customreprecipitated

Sources & evidence

ORD record
ord-b62156cf051240ef9ef518264adfce06
Source dataset
uspto-grants-1990_11
Patent number
US04968837

Reaction notes

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