Réaction #956

ord-d3631dc5ac684ec9b01dd5b9b7ce5987

Équation de réaction

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

Réactifs

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

Réactifs

Aucun

Solvants

CN(C)C=O
dimethylformamide

Conditions de réaction

Température
100°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONwas added
  2. 2
    Extractionextracted with ethyl acetate three times
  3. 3
    LavageThe combined organic phase was washed with water
  4. 4
    Séchagedried (Na2SO4)
  5. 5
    Autreevaporated
  6. 6
    Autrechromatographed on silica gel

Mode opératoire

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%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05723444uspto-grants-1998_03