N-Hydroxyphthalimide → HCID 58190542, compound

HRID 1959650Notes

Reaction equation

HRID 1959650 reaction equation
[O:1]1[CH2:4][CH:3]([OH:5])[CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:26]1[C:34](=[O:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]1=[O:36].N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>>[O:1]1[CH2:4][CH:3]([O:5][N:26]2[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:36])[CH2:2]1

Participants

5

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 9942117Oxetan-3-ol

Product 1

HCID 58190542HCID 58190542, compoundYield 13.5%

Procedure

To a solution of oxetan-3-ol (1.0 g, 13.50 mmol) were added triphenylphosphine (4.25 g, 16.20 mmol) and 2-hydroxyisoindoline-1,3-dione (2.42 g, 14.85 mmol). After stirring at rt for 10 min, (E)-diisopropyl diazene-1,2-dicarboxylate (3.28 g, 16.20 mmol) was added. After stirring at 30° C. overnight, the reaction mixture was quenched with NH4Cl (aq), extracted with EtOAc, washed with NH4Cl (aq), dried over Na2SO4, filtered and concentrated in vacuo to give the crude product, which was purified with column chromatography on silica gel (gradient hexanes:EtOAc) to give a colorless oil 2-(oxetan-3-yloxy)isoindoline-1,3-dione (400 mg, 6%). LCMS (method B): [MH]+=220, tR=1.67 min.

Workup

  1. stirringAfter stirring at 30° C. overnight
  2. customthe reaction mixture was quenched with NH4Cl (aq)
  3. extractionextracted with EtOAc
  4. washwashed with NH4Cl (aq)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude product, which
  9. customwas purified with column chromatography on silica gel (gradient hexanes:EtOAc)

Sources & evidence

ORD record
ord-05ef8a05b3104c11ba2867f4dc5b8f30
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

Loading…