2-(6-Azidohexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione → 2-(6-Aminohexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione

HRID 1053941Notes

Reaction equation

HRID 1053941 reaction equation
[N:1]([CH:4]1[CH:8]2[O:9][CH2:10][CH:11]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])[CH:7]2[O:6][CH2:5]1)=[N+]=[N-]>CO.[OH-].[OH-].[Pd+2]>[NH2:1][CH:4]1[CH:8]2[O:9][CH2:10][CH:11]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])[CH:7]2[O:6][CH2:5]1

Participants

4

Reactant 1

HCID 1183879722-(6-Azidohexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione

Product 1

HCID 1183879492-(6-Aminohexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(6-azidohexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione (crude product from above step) in MeOH (70 mL) was added 10% Pd(OH)2/C (240 mg, 0.17 mmol). The mixture was stirred at room temperature overnight under H2 atmosphere. The mixture was filtered, and the filtrate was concentrated in vacuo to give the crude product. The residue was used for the next step without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-721e187090ae42e5aa329ce99108bde2
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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