Reaction #927282

Reaction equation

4,5-epoxy-17-methyl-3-trifluoromethanesulfonyloxymorphinan-6-one

vinyltributyltin

LiCl

triphenylphosphine

→

NH4OH

title product

Yield 155.2%

4,5-Epoxy-17-methyl-3-vinylmorphinan-6-one

Yield 155.2%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONit was poured onto water
2. 2
   Extractionthe aqueous phase was extracted with AcOEt
3. 3
   DryingThe organic phase was dried over Na2SO4
4. 4
   Otherthe solvent was removed in vacuo
5. 5
   OtherThe crude reaction mixture
6. 6
   Otherwas purified by flash chromatography
7. 7
   Washeluting with a mixture CH2Cl2/MeOH/conc

Procedure

2 g (4.8 mmol) of 4,5-epoxy-17-methyl-3-trifluoromethanesulfonyloxymorphinan-6-one were dissolved, under a nitrogen atmosphere, in 25 ml of dimethylformamide, then 1.46 ml (5 mmol) of vinyltributyltin, 1.6 g (38.4 mmol) of LiCl, 0.337 g (0.48 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.5 g (1.9 mmol) of triphenylphosphine were added. The reaction mixture was heated to 100° C. for 3 h, then it was poured onto water and the aqueous phase was extracted with AcOEt. The organic phase was dried over Na2SO4 and the solvent was removed in vacuo. The crude reaction mixture was purified by flash chromatography, eluting with a mixture CH2Cl2/MeOH/conc. NH4OH 90:7:0.7 respectively, yielding 1.1 g of the title product.

Source