반응 #956

ord-d3631dc5ac684ec9b01dd5b9b7ce5987

반응 방정식

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

반응 조건

온도
100°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.ADDITIONwas added
  2. 2
    추출extracted with ethyl acetate three times
  3. 3
    세척The combined organic phase was washed with water
  4. 4
    건조dried (Na2SO4)
  5. 5
    기타evaporated
  6. 6
    기타chromatographed on silica gel

실험 절차

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%).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05723444uspto-grants-1998_03