تفاعل #956

ord-d3631dc5ac684ec9b01dd5b9b7ce5987

معادلة التفاعل

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

المذيبات

ظروف التفاعل

درجة الحرارة
100°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONwas added
  2. 2
    استخلاصextracted with ethyl acetate three times
  3. 3
    غسيلThe combined organic phase was washed with water
  4. 4
    تجفيفdried (Na2SO4)
  5. 5
    أخرىevaporated
  6. 6
    أخرىchromatographed on silica gel

الإجراء التجريبي

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%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05723444uspto-grants-1998_03