Ethyl Acetate → (3As,7as)-7,7-diphenylperhydroisoindol-4-one d-mandelate

HRID 2211401Notes

Reaction equation

HRID 2211401 reaction equation
[OH-:1].[Na+].Cl.[C:4]1([C:10]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:18]3[CH:14]([CH2:15][NH:16][CH2:17]3)[C:13](=[O:19])[CH2:12][CH2:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:26]([O:29]CC)(=[O:28])[CH3:27]>>[C:26]([OH:29])(=[O:28])[C@@H:27]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:1].[C:20]1([C:10]2([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[C@@H:18]3[C@@H:14]([CH2:15][NH:16][CH2:17]3)[C:13](=[O:19])[CH2:12][CH2:11]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

Product 1

HCID 131719175(3As,7as)-7,7-diphenylperhydroisoindol-4-one d-mandelate

Procedure

50 cm3 of aqueous 4N sodium hydroxide are slowly added to a suspension of 20 g of (3aRS,7aRS)-7,7-diphenyl-perhydroisoindol-4-one hydrochloride in 250 cm3 of ethyl acetate, while stirring; stirring is continued until the starting substance has disappeared. The organic solution is washed with 100 cm3 of distilled water and with 100 cm3 of a saturated solution of sodium chloride, dried over magnesium sulphate and filtered. A solution of 9.3 g of D-(-)mandelic acid in 50 cm3 of ethyl acetate is added to the solution thus obtained, while stirring. The crystals formed are filtered off, drained, washed with 50 cm3 of ethyl acetate (twice) and dried. The crystals are taken up in a solution of 220 cm3 of acetonitrile and 60 cm3 of distilled water and the mixture is refluxed for 15 minutes, while stirring; the crystals formed are filtered off and recrystallised in a mixture of 100 cm3 of acetonitrile and 35 cm3 of distilled water. 6.4 g of (3aS,7aS)-7,7-diphenyl-perhydroisoindol-4-one D-mandelate are obtained.

Workup

  1. stirringstirring
  2. washThe organic solution is washed with 100 cm3 of distilled water and with 100 cm3 of a saturated solution of sodium chloride
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. additionA solution of 9.3 g of D-(-)mandelic acid in 50 cm3 of ethyl acetate is added to the solution
  6. customthus obtained
  7. stirringwhile stirring
  8. customThe crystals formed
  9. filtrationare filtered off
  10. washwashed with 50 cm3 of ethyl acetate (twice) and
  11. customdried
  12. temperaturethe mixture is refluxed for 15 minutes
  13. stirringwhile stirring
  14. customthe crystals formed
  15. filtrationare filtered off
  16. customrecrystallised in a mixture of 100 cm3 of acetonitrile and 35 cm3 of distilled water

Sources & evidence

ORD record
ord-03448900437a4e96b81d3d11d11ae312
Source dataset
uspto-grants-1995_10
Patent number
US05463077

Reaction notes

Loading…