Phthalimide → HCID 58009522, compound

HRID 1009475Notes

Reaction equation

HRID 1009475 reaction equation
O[CH2:2][C:3]1[N:7]([CH3:8])[C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:18]=[C:16]1[C:15]2[C:14](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13](=[O:23])[N:17]1[CH2:2][C:3]1[N:7]([CH3:8])[C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58009357methyl 5-(hydroxymethyl)-1-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 58009522HCID 58009522, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

590 mg of methyl 5-(hydroxymethyl)-1-methyl-1H-pyrrole-2-carboxylate, 770 mg of phthalimide, and 1.83 g of triphenylphosphine were dissolved in 10.0 mL of THF, and 2.75 mL of diethyl azodicarboxylate was added thereto under ice-cooling, followed by stirring at room temperature overnight. The reaction liquid was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1) to obtain 650 mg of methyl 5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1-methyl-1H-pyrrole-2-carboxylate.

Workup

  1. temperatureunder ice-cooling
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-7d3aafdd05de4c45ab9f5c2b1d2ad71d
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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