Cornforth reagent → (7aS)-2-(3,5-dichloro-phenyl)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3,6-trione

HRID 49978

Reaction equation

HRID 49978 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@H:12]3[CH2:15][C@@H:16]([OH:18])[CH2:17][N:11]3[C:10]2=[O:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@H:12]3[CH2:15][C:16](=[O:18])[CH2:17][N:11]3[C:10]2=[O:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 58840802(6R,7aS)-2-(3,5-dichlorophenyl)-6-hydroxytetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione

Product 1

HCID 21301015(7aS)-2-(3,5-dichloro-phenyl)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3,6-trione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (7aS,6R)-2-(3,5-dichloro-phenyl)-6-hydroxy-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione (11.3 g) (0.038 mol) (Preparation 2), in 185 mL of DCM was added molecular sieves 3A (18 g) then PDC (33.5 g) (0.093 mol). The reaction mixture was stirred for 72 h at RT, then the insoluble material eliminated. After evaporating the solvent, the residue was purified by SiO2 chromatography (eluent: DCM/EtOAc 95/5) to afford the titled compound as a white solid (7.3). NMR (CDCl3, 200 MHz): 7.45-7.35 (3H, m), 4.65 (1H, dd), 4.25 (1H, dd), 3.12 (1H, dd), 2.97 (1H, dd), 2.65 (1H, dd).

Workup

  1. customAfter evaporating the solvent
  2. customthe residue was purified by SiO2 chromatography (eluent: DCM/EtOAc 95/5)

Sources & evidence

ORD record
ord-389441f5125d41afac79ea133eed6229
Source dataset
uspto-grants-2004_03
Patent number
US06710064B2

Linked notes

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