Reaktion #956

ord-d3631dc5ac684ec9b01dd5b9b7ce5987

Reaktionsgleichung

CS(=O)(=O)OCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1
1-benzyloxycarbonylamidino-4-mesyloxyethyl piperidine
[N-]=[N+]=[N-].[Na+]
sodium azide
O
water
→
[N-]=[N+]=NCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1
4-Azidoethyl-1-benzyloxycarbonylamidino piperidine

Edukte

CS(=O)(=O)OCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1
1-benzyloxycarbonylamidino-4-mesyloxyethyl piperidine
[N-]=[N+]=[N-].[Na+]
sodium azide
O
water

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide

Reaktionsbedingungen

Temperatur
100°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas added
  2. 2
    Extraktionextracted with ethyl acetate three times
  3. 3
    WaschenThe combined organic phase was washed with water
  4. 4
    Trocknendried (Na2SO4)
  5. 5
    Sonstigeevaporated
  6. 6
    Sonstigechromatographed on silica gel

Vorschrift

In 100 ml of dimethylformamide was dissolve (0.0115 mol) of crude 1-benzyloxycarbonylamidino-4-mesyloxyethyl piperidine and 4.5 g (0.069 mol) of sodium azide was added. The mixture was heated at 100° C. for 2.5 h. It was then poured into water and extracted with ethyl acetate three times. The combined organic phase was washed with water, dried (Na2SO4) and evaporated. The residue was flash chromatographed on silica gel using ethyl acetate/heptane 1/1 as eluent. Yield: 3.0 g (79%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723444uspto-grants-1998_03