Potassium bisulfate → HCID 178515016, compound

HRID 1269785Notes

Reaction equation

HRID 1269785 reaction equation
[N+](C1C=CC(C([O:10][C@H:11]2[CH2:16][CH2:15][C@@H:14]([N:17]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]3=[O:27])[CH2:13][CH2:12]2)=O)=CC=1)([O-])=O.C[O-].[Na+].S([O-])(O)(=O)=O.[K+]>CO.O1CCCC1>[OH:10][C@@H:11]1[CH2:12][CH2:13][C@H:14]([N:17]2[C:18](=[O:27])[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]2=[O:26])[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 516920Potassium bisulfateHCID 10942334Sodium MethoxideHCID 178525746HCID 178525746, compound

Product 1

HCID 178515016HCID 178515016, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of cis-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)cyclohexyl 4-nitrobenzoate (2.0 g, 5.07 mmol) in a mixture of methanol (40 ml) and tetrahydrofuran (40 ml) was added 28%-sodium methoxide (1.04 ml, 5.07 mmol) at 0° C., and stirred at 0° C. for 30 minutes and then at room temperature for 3.5 hours. The reaction solution was adjusted to pH 4 with a 0.5M-aqueous potassium hydrogensulfate solution and distilled under reduced pressure to remove the solvent. The residue was added to water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=3/1) to obtain cis-2-(4-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione (932 mg, 75%).

Workup

  1. waitat room temperature for 3.5 hours
  2. distillationdistilled under reduced pressure
  3. customto remove the solvent
  4. additionThe residue was added to water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-a08001a38c0848eeaecca2a72777619d
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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