Reaktion #10521

ord-93eff2bf0daa450c897e724582f37625

Reaktionsgleichung

CC(C)(C)OC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C(N)=O)N2C1=O
tert-butyl ((2R,5S,7aS)-5-carbamoyl-3-oxohexahydropyrrolizin-2-yl)carbamate
Clc1nc(Cl)nc(Cl)n1
cyanuric chloride
→
CC(C)(C)OC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C#N)N2C1=O
tert-butyl ((2R,5S,7aS)-5-cyano-3-oxohexahydropyrrolizin-2-yl)carbamate

Edukte

CC(C)(C)OC(=O)N[C@@H]1C[C@@H]2CC[C@@H](C(N)=O)N2C1=O
tert-butyl ((2R,5S,7aS)-5-carbamoyl-3-oxohexahydropyrrolizin-2-yl)carbamate
Clc1nc(Cl)nc(Cl)n1
cyanuric chloride

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe dimethylformamide was removed in vacuo
  2. 2
    SonstigeThe residue was chromatographed on silica gel

Vorschrift

100 mg of tert-butyl ((2R,5S,7aS)-5-carbamoyl-3-oxohexahydropyrrolizin-2-yl)carbamate were dissolved in 2 ml of dimethylformamide, and 65 mg of cyanuric chloride were added. The mixture was stirred for 3 h, and the dimethylformamide was removed in vacuo. The residue was chromatographed on silica gel.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07094800B2uspto-grants-2006_08