Reaktion #1244262

ord-f01e0fb09ffc4f4e9e7ee22879eae9b7

Reaktionsgleichung

O=C1O[C@H]([C@@H](O)CO)C([O-])=C1O.[Na+]
sodium ascorbate
C#CCn1ccnc1[N+](=O)[O-]
nitropropyne
C#CCn1ccnc1[N+](=O)[O-]
2-Nitro-1-(prop-2-ynyl)-1H-imidazole
CC(O)N=[N+]=[N-]
azido ethanol
→
O=[N+]([O-])c1nccn1Cc1cn(CCO)nn1
11
Ausbeute 76.3%
O=[N+]([O-])c1nccn1Cc1cn(CCO)nn1
2-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethanol
Ausbeute 76.3%

Edukte

O=C1O[C@H]([C@@H](O)CO)C([O-])=C1O.[Na+]
sodium ascorbate
C#CCn1ccnc1[N+](=O)[O-]
nitropropyne
C#CCn1ccnc1[N+](=O)[O-]
2-Nitro-1-(prop-2-ynyl)-1H-imidazole
CC(O)N=[N+]=[N-]
azido ethanol

Reagenzien

O=S(=O)([O-])[O-].[Cu+2]
CuSO4

Lösungsmittel

CO
MeOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONthe reaction was poured onto EtOAc
  2. 2
    Waschenwashed with NH4OH
  3. 3
    Sonstigethe residue was purified on a combiflash system

Vorschrift

To a round bottom flask was added nitropropyne 10 (150 mg, 0.99 mmol) and azido ethanol (86 mg, 0.99 mmol). To this flask was added CuSO4 (0.04M, 100 uL) and sodium ascorbate (0.1 M, 100 uL). After 16 hrs, the reaction was poured onto EtOAc and washed with NH4OH. The organics were combined and the residue was purified on a combiflash system using EtOAc:Hex as the eluent followed by DCM:MeOH to afford 180 mg (76.3% yield) of 11 as a clear colorless oil. Mass Spec (lo-res): Calc'd for C8H10N6O3: 238.08; found: 239.10 (M+H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07807394B2uspto-grants-2010_10