Phthalimide → 2-(1-(Pyridin-4-yl)ethyl)isoindoline-1,3-dione

HRID 2092012Notes

Reaction equation

HRID 2092012 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7](O)[CH3:8])=[CH:3][CH:2]=1.[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(OCC)(=O)C.O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([N:14]2[C:10](=[O:20])[C:11]3[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]2=[O:15])[CH3:8])=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 90919alpha-Methyl-4-pyridinemethanol

Product 1

HCID 595742662-(1-(Pyridin-4-yl)ethyl)isoindoline-1,3-dioneYield 48.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A tetrahydrofuran solution (10 mL) of 1-(pyridin-4-yl)ethanol (283 mg, 2.32 mmol), phthalimide (375 mg, 2.55 mmol) and triphenylphosphine (686 mg, 2.55 mmol) was mixed with diisopropyl azodicarboxylate (40% in toluene, 1.34 mL, 2.55 mmol) and stirred at room temperature for 29 hours. After completion of the reaction, the reaction solution was mixed with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform/ethyl acetate=10/1) to give the desired product (283 mg, 48% yield).

Workup

  1. customAfter completion of the reaction
  2. washthe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-c424dab90e744a1d8a0b1dec643ad510
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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