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

HRID 49978

반응식

HRID 49978 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-389441f5125d41afac79ea133eed6229
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710064B2

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