8-(bromomethyl)-1,4-dioxaspiro[4.5]decane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1 g of 3-(2-Methoxyphenyl)pyrrolidine is dissolved in 60 ml of dioxane and 0.85 g Nal, followed by 1.2 ml of N,N-ethyldiisopropylamine and 1.5 g of 8-bromomethyl-1.4-dioxaspiro[4.5]decane, dissolved in 5 ml of dioxane, are added. The reaction mixture is stirred overnight at 80°, evaporated and the residue extracted with ethylacetate/2N Na2CO3, followed by aqueous NaCl. The combined, dried and evaporated organic phases yields an oily residue which is purified by flash chromatography on silica gel using t-butylmethylether as a solvent system providing the product as an oil. MS (EI): M+=331; NMR (DMSO): 1.1 (2H, m), 1.45 (3H, m), 1.6-1.8 (5H, m), 2.15 (1H, m), 2.25 (2H, m), 2.4 (1H, t), 2.6 (2H, m), 2.8 (1H, t), 3.6 (1H, t), 3.75 (3H, s), 3.85 (4H, s), 6.9 (2H, dd), 7.15 (1H, t), 7.3 (1H, d). are added evaporated the residue extracted with ethylacetate/2N Na2CO3 dried evaporated organic phases yields an oily residue which is purified by flash chromatography on silica gel