Potassium Permanganate → HCID 86701853, compound

HRID 1844092Notes

Reaction equation

HRID 1844092 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[CH2:11][CH:10]2[CH2:14][C:15]3[C:20]([CH:9]12)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-:21][Mn](=O)(=O)=O.[K+]>CC(C)=O.O>[O:13]=[C:12]1[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@@H:9]2[C:20]3[C:15]([C:14](=[O:21])[C@@H:10]2[CH2:11]1)=[CH:16][CH:17]=[CH:18][CH:19]=3

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 67975594HCID 67975594, compound

Product 1

HCID 86701853HCID 86701853, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 2-oxo-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]pyrrole-1-carboxylic acid tert-butyl ester F1 (5.00 g, 18.2 mmol) in acetone (90 mL) and water (20 mL) was added KMnO4 (14.7 g, 93 mmol). The solution was stirred for 48 h at room temperature and filtered. The solution was concentrated to half the volume and sodium thiosulfate solution was added (2%, 50 mL). The solution was extracted with ethylacetate, washed with brine, dried and concentrated. The residue was purified by flash chromatography eluting with cyclohexane and ethyl acetate (7/3) to give the desired product F26 (1.6 g, 30%). LCMS (method E): 0.81 min; ES+: 597 (2M+Na+).

Workup

  1. filtrationfiltered
  2. concentrationThe solution was concentrated to half the volume and sodium thiosulfate solution
  3. additionwas added (2%, 50 mL)
  4. extractionThe solution was extracted with ethylacetate
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. washeluting with cyclohexane and ethyl acetate (7/3)

Sources & evidence

ORD record
ord-9b7691bb3d2f46e8b46313e9a31b719a
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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