Tributylstannane → 1'-Methyl-2H-spiro[benzofuran-3,4'-piperidine]

Participants

Reaction Steps

4-(2-Iodophenoxymethyl)-1-methyl-1,2,3,6-tetrahydropyridine (D2, 8.72 g, 0.026 mol) and AIBN (0.20 g, 0.0012 mol) were stirred at reflux under Ar in benzene (500 ml) as tributyltin hydride (14.3 ml, 0.053 mol) was added dropwise in benzene (100 ml) over 1 h. The mixture was stirred at reflux for a further 4.5 h, cooled and evaporated. The residue was dissolved in ethyl acetate, and extracted with dil. HCl. The extract was basified (sat. K2CO3 solution) and extracted with ethyl acetate. This organic extract was dried (Na2SO4) and evaporated to give a brown solid, which was chromatographed on silica gel, eluting with 0-8% methanol/chloroform (gradient) to give the title compound (3.86 g, 69%) as a light yellow solid.

Provenance & Evidence