反应详情

1-Phenyl-cycloheptanecarboxylic acid methyl ester (Example 1d) (1.0 g) and (R)-quinuclidin-3-ol (0.39 g) were refluxed in heptane (50 mL) containing sodium (˜5 mg in a Dean and Stark apparatus for 24 hours. Heptane (20 mL) was replaced with toluene (20 mL) and the reflux was continued for 3 days. The reaction was partitioned between water (50 mL) and ether (50 mL) and the ether layer was separated, dried (MgSO4) and evaporated. The crude product was purified by column chromatography on silica elutting with ethyl acetate/triethylamine (99/1) to afford the titled compound as an oil (0.83 g).

1. customThe reaction was partitioned between water (50 mL) and ether (50 mL)
2. customthe ether layer was separated
3. dry with materialdried (MgSO4)
4. customevaporated
5. customThe crude product was purified by column chromatography on silica elutting with ethyl acetate/triethylamine (99/1)