PREPARATION OF CYCLOPROPANE DERIVATIVE

Using NaH and Pd(0)

Procedure

1.    Dissolve Imine and butene in THF.  Stir (N₂)

2.    Add Pd(OAc)₂ and Ph₃P (as neat to form Pd(0)) [1]

3.    Stir the mixture at R.T. for 30 min

4.    Add slowly and portionally NaH (60% in mineral oil) over 45 min [2]

5.    Stir the reaction mixture at R.T for 1 hr [3]

6.    Quench reaction w/ ice cold water and dilute w/ EtOAc

7.    Filter thru Celite [4].   Wash filtrate w/water and brine

8.    Dry organic layer w/ MgSO₄.  Filter

9.    Concentrate in vacuo ® crude as brownish oil

10.           Chromatograph w/ 0% ® 5% EtOAc/Hex [5]

11.           NMR w/ CDCl₃.  Yield 70% as yellow oil [6]