Cyanuric chloride → Tert-butyl ((2r,5s,7as)-5-cyano-3-oxohexahydropyrrolizin-2-yl)carbamate

HRID 10425

Reaction equation

HRID 10425 reaction equation
[C:1]([C@@H:4]1[CH2:11][CH2:10][C@@H:9]2[N:5]1[C:6](=[O:20])[C@H:7]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:8]2)(=O)[NH2:2].N1C(Cl)=NC(Cl)=NC=1Cl>CN(C)C=O>[C:1]([C@@H:4]1[CH2:11][CH2:10][C@@H:9]2[N:5]1[C:6](=[O:20])[C@H:7]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:8]2)#[N:2]

Participants

4

Reactant 2

HCID 7954Cyanuric chlorideHCID 90895673HCID 90895673, compound

Product 1

HCID 91321587Tert-butyl ((2r,5s,7as)-5-cyano-3-oxohexahydropyrrolizin-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. customthe dimethylformamide was removed in vacuo
  2. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-93eff2bf0daa450c897e724582f37625
Source dataset
uspto-grants-2006_08
Patent number
US07094800B2

Linked notes

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