Sodium Hydroxide → (3aRS,7aRS)-7,7-Diphenylperhydro-4-isoindolone

HRID 1029916Notes

Reaction equation

HRID 1029916 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>ClCCl>[C:20]1([C:10]2([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:18]3[CH: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 2

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

Product 1

HCID 21264544(3aRS,7aRS)-7,7-Diphenylperhydro-4-isoindoloneYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4N aqueous sodium hydroxide solution (100 cc) is added to a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (16.6 g) in dichloromethane (250 cc), with stirring; the organic phase is dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (4 kPa). (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone (13 g) is obtained in the form of a white meringue.

Workup

  1. dry with materialthe organic phase is dried over magnesium sulphate
  2. filtrationfiltered
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure (4 kPa)

Sources & evidence

ORD record
ord-d5466c0e48df40dda68daa492f1d73ff
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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