Maleimide → 4-(Tert.-butyloxycarbonylamino)-1,3-dioxo-1,3,3a,4,7,7a-hexahydroisoindole

HRID 2209978Notes

Reaction equation

HRID 2209978 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH:3]=[CH:2]1.[C:8]([O:12][C:13]([NH:15][CH:16]=[CH:17][CH:18]=[CH2:19])=[O:14])([CH3:11])([CH3:10])[CH3:9]>O1CCCC1>[C:8]([O:12][C:13]([NH:15][CH:16]1[CH:17]=[CH:18][CH2:19][CH:3]2[CH:2]1[C:1](=[O:7])[NH:5][C:4]2=[O:6])=[O:14])([CH3:10])([CH3:11])[CH3:9]

Participants

4

Reactant 2

HCID 10935MaleimideHCID 22897234Tert-butyl N-buta-1,3-dienylcarbamate

Product 1

HCID 193714494-(Tert.-butyloxycarbonylamino)-1,3-dioxo-1,3,3a,4,7,7a-hexahydroisoindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

48.8 g (0.5 mol) of maleimide dissolved in 200 ml of absolute tetrahydrofuran are initially introduced, and 120 g (0.5 mol) of approximately 70% 1-(tert.-butyloxycarbonylamino)-1,3-butadiene in the form of a solution in 500 ml of absolute tetrahydrofuran are added dropwise, the temperature being maintained at 20° to 30° C. Stirring is continued overnight at room temperature. The mixture is then concentrated and recrystallized from ethyl acetate. This gives 57 g of product with a melting point of 177° to 182° C. A further 13 g with a melting point of 158° to 160°C. are obtained from the mother liquor.

Workup

  1. additionare initially introduced
  2. temperaturethe temperature being maintained at 20° to 30° C
  3. concentrationThe mixture is then concentrated
  4. customrecrystallized from ethyl acetate
  5. customA further 13 g with a melting point of 158° to 160°C. are obtained from the mother liquor

Sources & evidence

ORD record
ord-356151e5c0ae4df5ad262fdaca129dd8
Source dataset
uspto-grants-1995_10
Patent number
US05457104

Reaction notes

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