178419-46-0Relevant articles and documents
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 α7 nicotinic receptor agonist
Macor, John E.,Mullen, George,Verhoest, Patrick,Sampognaro, Anthony,Shepardson, Bruce,Mack, Robert A.
, p. 6493 - 6495 (2004)
A direct, short chiral synthesis of the selective α7 nicotinic receptor agonist (-)-spiro[1-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.