1,1'-Carbonyldiimidazole → (S)-hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one

HRID 734611Notes

Reaction equation

HRID 734611 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][NH:4]1.[C:8](N1C=CN=C1)(N1C=CN=C1)=[O:9]>C(Cl)Cl>[CH2:2]1[NH:1][C:8](=[O:9])[N:4]2[CH2:5][CH2:6][CH2:7][C@@H:3]12

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 2734054(S)-(+)-2-(Aminomethyl)pyrrolidine

Product 1

HCID 14358392(S)-hexahydro-3H-pyrrolo[1,2-c]imidazol-3-oneYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(Aminomethyl)pyrrolidine (250 mg) and carbonyldiimidazole (400 mg, 1.0 equiv.) were dissolved in DCM (50 mL). The resulting mixture was stirred at room temperature for 18 hours, then concentrated under vacuum. The residue was purified by flash column chromatography (SPE cartridge, SiO2), using DCM-methanol (95:5) as eluent to afford the title compound as colourless solid (150 mg, 50% yield).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by flash column chromatography (SPE cartridge, SiO2)

Sources & evidence

ORD record
ord-7fcdbd540477438fa60ffdfa33d57c01
Source dataset
uspto-grants-2009_09
Patent number
US07592346B2

Reaction notes

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