(+-)-3-Quinuclidinol → HCID 19038078, compound

Participants

Reaction Steps

A solution of 1.96 g of 3-quinuclidinol in 30 ml of dimethylformamide was cooled to 5° C. in an atmosphere of nitrogen. 0.67 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was then added to the cooled solution, and then the solution was stirred at room temperature for 30 minutes. At the end of this time, the reaction mixture was cooled to 5° C., and 3.0 g of 3,4-dichloro-5-phenylisoxazole were added. The resulting mixture was then stirred at room temperature for 5 hours. At the end of this time, it was poured into 100 ml of ice-water and extracted twice, each time with 100 ml of ethyl acetate. The ethyl acetate extracts were combined and washed twice, each time with 100 ml of a 10% w/v aqueous solution of sodium chloride; they were then dried over anhydrous magnesium sulfate, after which the drying agent was removed by filtration. The solvent was then removed from the filtrate by distillation under reduced pressure. The residue thus obtained was purified by column chromatography through silica gel using a 10:1 by volume mixture of ethyl acetate and methanol as the eluent, to afford 4.21 g (yield 98.7%) of the title compound as a colorless and transparent oil.

Provenance & Evidence