Water → HCID 131717361, compound

HRID 1196266Notes

Reaction equation

HRID 1196266 reaction equation
[OH-].[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]([OH:36])(=[O:35])[C@H:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[OH:28].O>C(OCC)(=O)C>[C:26]([OH:36])(=[O:35])[C@H:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[OH:28].[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

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 439616(S)-mandelic acidHCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

Product 1

HCID 131717361HCID 131717361, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

4N aqueous sodium hydroxide (500 cc) is added slowly and with stirring to a suspension of (3aRS,7aRS)-7,7-diphenylperhydro-4-isoindolone hydrochloride (200 g) in ethyl acetate (2000 cc); stirring is continued until the starting material has disappeared. The organic solution is washed with distilled water (250 cc) and with saturated aqueous sodium chloride solution (250 cc), dried over magnesium sulphate and filtered. To the solution thereby obtained, a solution of L(+)-mandelic acid (92.8 g) in ethyl acetate (1000 cc) is added with stirring; after 4 hours' stirring, the crystals obtained are drained, crystals are taken up with distilled water (2000 cc); the mixture is heated to reflux with stirring for 15 minutes; the insoluble crystals are drained, washed with distilled water (2×100 cc) and dried. They are recrystallized in a mixture of acetonitrile (1100 cc) and distilled water (500 cc); the crystals obtained are drained, washed with acetonitrile (3×40 cc) and dried. (3aR,7aR)-7,7-Diphenylperhydro-4-isoindolone L-mandelate (80 g) is obtained; [α]D20 =-164° (c=1, methanol).

Workup

  1. washThe organic solution is washed with distilled water (250 cc) and with saturated aqueous sodium chloride solution (250 cc)
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customTo the solution thereby obtained
  5. stirringwith stirring
  6. stirringafter 4 hours' stirring
  7. customthe crystals obtained
  8. temperaturethe mixture is heated
  9. temperatureto reflux
  10. stirringwith stirring for 15 minutes
  11. washwashed with distilled water (2×100 cc)
  12. customdried
  13. customThey are recrystallized in a mixture of acetonitrile (1100 cc)
  14. distillationdistilled water (500 cc)
  15. customthe crystals obtained
  16. washwashed with acetonitrile (3×40 cc)
  17. customdried

Sources & evidence

ORD record
ord-5e2e957e0dd541e69072011d11c5b2fd
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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