Reaction #960

ord-8f9821df03a7466091a3423b9a248655

Reaction equation

CS(=O)(=O)OCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1
(3RS)-1-(N-benzyloxycarbonylamidino)-3-mesyloxymethyl pyrrolidine
[N-]=[N+]=[N-].[Na+]
sodium azide
O
Water
→
[N-]=[N+]=NCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1
product
Yield 68.2%
[N-]=[N+]=NCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1
(3RS)-1-(N-benzyloxycarbonylamidino)-3-azidomethyl pyrrolidine
Yield 68.2%

Reactants

CS(=O)(=O)OCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1
(3RS)-1-(N-benzyloxycarbonylamidino)-3-mesyloxymethyl pyrrolidine
[N-]=[N+]=[N-].[Na+]
sodium azide
O
Water

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Temperature
60°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractionthe mixture was extracted twice with toluene/ethyl acetate 2/1
  2. 2
    DryingThe combined organic layer was dried (Na2SO4)
  3. 3
    Filtrationfiltered
  4. 4
    Otherevaporated
  5. 5
    OtherThe crude product was purified by flash chromatography

Procedure

0.450 g (1.27 mmole) (3RS)-1-(N-benzyloxycarbonylamidino)-3-mesyloxymethyl pyrrolidine and 0.124 g (1.9 mmole) of sodium azide were dissolved in 10 ml dimethylformamide and heated to 60° C. for four hours followed by stirring at room temperature over night. Water was added and the mixture was extracted twice with toluene/ethyl acetate 2/1. The combined organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography using CH2Cl2 /MeOH 95/5 as eluent to yield 0.262 g (68%) of the product.

Source

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