Reacción #956

ord-d3631dc5ac684ec9b01dd5b9b7ce5987

Ecuación de reacción

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

Reactantes

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

Reactivos

Ninguno

Disolventes

CN(C)C=O
dimethylformamide

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONwas added
  2. 2
    Extracciónextracted with ethyl acetate three times
  3. 3
    LavadoThe combined organic phase was washed with water
  4. 4
    Secadodried (Na2SO4)
  5. 5
    Otroevaporated
  6. 6
    Otrochromatographed on silica gel

Procedimiento

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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723444uspto-grants-1998_03