N-Hydroxyphthalimide → HCID 13247966, compound

HRID 661726Notes

Reaction equation

HRID 661726 reaction equation
[N:1]1[CH:5]=[C:4]([CH:6]=[O:7])[NH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O[N:34]1[C:38](=[O:39])[C:37]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]2[C:35]1=[O:44].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[N:1]1[CH:5]=[C:4]([CH2:6][O:7][N:34]2[C:38](=[O:39])[C:37]3[C:36](=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:35]2=[O:44])[NH:3][CH:2]=1

Participants

7

Reactant 5

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 764281H-Imidazole-4-carbaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 13247966HCID 13247966, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(3H-Imidazol-4-yl)-methanol (90 mg, 0.92 mmol) obtained by reducing 3H-imidazole-4-carboaldehyde (commercial product) with lithium aluminum hydride in THF was mixed with PPh3 (245 mg, 0.94 mmol), N-hydroxy-phthalimide (153 mg, 0.94 mmol), and diisopropyl azodicarboxylate (189 mg, 0.94 mmol) in anhydrous THF at 0° C. under a nitrogen atmosphere, and the mixture was stirred. After 4 hours, the reaction mixture was purified by silica gel chromatography to give 2-(3H-imidazol-4-ylmethoxy)-isoindol-1,3-dione (30 mg).

Workup

  1. customthe reaction mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-42ebbd24de644dd495ed05f2daf20b83
Source dataset
uspto-grants-2011_12
Patent number
US08084645B2

Reaction notes

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