HCID 178523771, compound → HCID 178519307, compound

HRID 22950Notes

Reaction equation

HRID 22950 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([N:20]2[CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([CH2:29][OH:30])[CH:26]=3)[CH2:21]2)=[O:19])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([N:20]2[CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([CH:29]=[O:30])[CH:26]=3)[CH2:21]2)=[O:19])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 178523771HCID 178523771, compound

Product 1

HCID 178519307HCID 178519307, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

20 g of manganese dioxide was added to 120 ml of a chloroform solution containing 4.0 g of N-benzyloxycarbonyl-trans-4-[(5-hydroxymethyl-2-isoindolinyl)carbonyl]cyclohexylamine, and the mixture was stirred at room temperature for 4 hours. Manganese dioxide was removed by filtration through Celite and the solvent was removed under reduced pressure. The residue was suspended in hexane-ethyl acetate and the crystals were collected by filtration to obtain N-benzyloxycarbonyl-trans-4-[(5-formyl-2-isoindolinyl)carbonyl]cyclohexylamine.

Workup

  1. customManganese dioxide was removed by filtration through Celite
  2. customthe solvent was removed under reduced pressure
  3. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-3ec4e80e1edf430a8ee4eedd99c59306
Source dataset
uspto-grants-2005_02
Patent number
US06849622B2

Reaction notes

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