1-Chloroethyl chloroformate → 2-Benzyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dione

HRID 2115278Notes

Reaction equation

HRID 2115278 reaction equation
ClC(OC(Cl)=O)C.[CH2:8]([N:15]1[C:22](=[O:23])[CH:21]2[CH:17]([CH2:18][N:19](CC3C=CC=CC=3)[CH2:20]2)[C:16]1=[O:31])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[CH2:8]([N:15]1[C:16](=[O:31])[CH:17]2[CH:21]([CH2:20][NH:19][CH2:18]2)[C:22]1=[O:23])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 218676822,5-Dibenzyltetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione

Product 1

HCID 129585072-Benzyltetrahydropyrrolo[3,4-c]pyrrole-1,3-dioneYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloroethylchloroformate (3.24 mL) was added dropwise to a solution of compound 1 (5.22 g) in dichloromethane (75 mL) at 0° C. The solution was then heated to reflux for 3 hours, cooled to room temperature and concentrated in vacuo. The residue was then dissolved in methanol (75 mL) and heated to reflux for another 3 hours. The mixture was cooled to 0° C. and ether (200 mL) was added. Filtration afforded the title compound 2 as a white solid (3.38 g, 90%). LCMS: Rf: 0.380 min, M+H+: 231.

Workup

  1. temperatureThe solution was then heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was then dissolved in methanol (75 mL)
  5. temperatureheated
  6. temperatureto reflux for another 3 hours
  7. temperatureThe mixture was cooled to 0° C.
  8. additionether (200 mL) was added
  9. filtrationFiltration

Sources & evidence

ORD record
ord-7ab8c251c328483aa03d551f12e9fa9d
Source dataset
uspto-grants-2008_10
Patent number
US07435830B2

Reaction notes

Loading…