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A chiral synthesis of (-)-spiro[1-azabicyclo[2.2.2] octane-3,5 ‘-oxazolidin-2 ‘-one]: A conformationally restricted analogue of acetylcholine that is a potent and selective alpha 7 nicotinic receptor agonist

A direct, short chiral synthesis of the selective 0 nicotinic receptor agonist (-)-spiro[l-azabicyclo[2.2.2]octane-3,5′-oxazolidin-2’-one] (AR-R17779) is presented. The key step utilized attack of the dianion of the (R)-HYTRA ester [(R)-(+)-2-hydroxy-1,2,2-triphenylethyl acetate] on quinuclidin-3-one, followed by a selective precipitation of the diasteriomeric tertiary alcohol that led to (S)-(-)-AR-R17779 in two additional steps.

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Reference:
Quinuclidine – Wikipedia,
,Quinuclidine | C7H13N | ChemSpider