Water → HCID 67071138, compound

HRID 1850922Notes

Reaction equation

HRID 1850922 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][C:18]([O:27][CH:28]([CH3:30])[CH3:29])=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=3)[CH:15]2[OH:31])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:15](=[O:31])[C:16]3[C:21](=[CH:20][C:19]([N+:24]([O-:26])=[O:25])=[C:18]([O:27][CH:28]([CH3:29])[CH3:30])[CH:17]=3)[C:22]2=[O:23])[CH2:12][CH2:13]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24503Dichromate ionHCID 59764484HCID 59764484, compound

Product 1

HCID 67071138HCID 67071138, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 4-(1-hydroxy-6-isopropoxy-5-nitro-3-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester from the previous step (173.9 mg, 0.4 mmol) in DMF (4 mL) is added pyridinum dichromate (286.5 mg, 0.8 mmol) in one portion. After stirring at room temperature for 2 h, the reaction mixture is poured into 25 mL of water and the product is extracted with EtOAc. The organic extracts are dried over Na2SO4, filtered and concentrated in vacuo to give crude 4-(5-isopropoxy-6-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester, which is directly used in the next step without further purification.

Workup

  1. extractionthe product is extracted with EtOAc
  2. dry with materialThe organic extracts are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-717e891a01dd435198dfb15c07658668
Source dataset
uspto-grants-2015_02
Patent number
US08957081B2

Reaction notes

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