Water → HCID 66970476, compound

HRID 1363219Notes

Reaction equation

HRID 1363219 reaction equation
[C@H:1]1([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.O.[O-:23][Mn](=O)(=O)=O.[K+]>CC(C)=O>[O:23]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@H:1]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 70160162-[(1R)-1,2,3,4-Tetrahydro-1-naphthalenyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 66970476HCID 66970476, compoundYield 3.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (R)-2-(1,2,3,4-tetrahydronaphthalen-1-yl)isoindoline-1,3-dione (3.9 g) in acetone (60 mL) at 0° C. was added MgSO4.7H2O (11.5 g) and water (20 mL). Then KMnO4 (11.5 g) was added portionwise over the period of 2 h and stirring continued at room temperature overnight. The brown solid was filtered off and the filtrate treated with saturated sodium metabisulfite, filtered, and extracted with CH2Cl2. The combined organic layer was washed with distilled water and saturated brine, dried over MgSO4, and concentrated in vacuo. The resultant was chromatographed on silica gel (EtOAc/hexane, 25/75) to afford 0.14 g of the title compound.

Workup

  1. filtrationThe brown solid was filtered off
  2. additionthe filtrate treated with saturated sodium metabisulfite
  3. filtrationfiltered
  4. extractionextracted with CH2Cl2
  5. washThe combined organic layer was washed with distilled water and saturated brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant was chromatographed on silica gel (EtOAc/hexane, 25/75)

Sources & evidence

ORD record
ord-0a9259a9c44e4a6fb14f4a6445282c5e
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

Loading…