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

HRID 49978

反応式

HRID 49978 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-389441f5125d41afac79ea133eed6229
出典データセット
uspto-grants-2004_03
特許番号
US06710064B2

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