3-Quinuclidinol, (-)- → HCID 58348365, compound

Participants

Reaction Steps

1-(3-Fluoro-phenyl)-cycloheptanecarboxylic acid methyl ester (Example 12c) (0.280 g) was dissolved in toluene (100 mL) and (R)-quinuclidin-3-ol (0.320 g) was added. Toluene (10 mL) was distilled off in a Dean and Stark apparatus and after cooling sodium hydride (10 mg) was added. The reaction was refluxed in a Dean and Stark apparatus for 4 hours after which time an extra amount of sodium hydride (10 mg) was added and the reaction was heated to reflux for a further 4 hours. After allowing to cool to room temperature, the toluene was washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluting with ethyl acetate/isohexane/triethylamine (50/50/ 1) then ethyl acetate/triethylamine (99/1) to afford the sub-titled compound (0.200 g

Provenance & Evidence