tert-butyl N-(4-aminobutyl)carbamate → 1-(4-N-Boc-aminobutyl)-1H-pyrrole-2,5-dione

HRID 16038

Reaction equation

HRID 16038 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:14]1(=O)[O:19][C:17](=[O:18])[CH:16]=[CH:15]1>C1(C)C=CC=CC=1>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:17](=[O:18])[CH:16]=[CH:15][C:14]1=[O:19])([CH3:5])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 7923Maleic Anhydride

Product 1

HCID 597091391-(4-N-Boc-aminobutyl)-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-BOC-1,4-diaminobutane (8.324 g, 0.044 mol) in dry toluene (50 ml) was added maleic anhydride (4.336 g, 0.044 mol) and the solution heated at reflux under Dean-Stark conditions for two days. The solvent was removed and the residue purified by silica column chromatography eluting with 25-40% ethyl acetate in hexane to give the title compound, 1.461 g, 12%, as a white solid.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux under Dean-Stark conditions for two days
  3. customThe solvent was removed
  4. customthe residue purified by silica column chromatography
  5. washeluting with 25-40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5f8e5d07e27c4cbb8e72a0fb83256796
Source dataset
uspto-grants-2010_06
Patent number
US07736635B2

Linked notes

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