3-Quinuclidinol, (-)- → 2-Cyclohexyl-2-fur-2-yl-2-hydroxyacetic Acid (3R)-1-azabicyclo[2.2.2]oct-3-yl Ester

Participants

Reaction Steps

Prepared using the same method as for Intermediate I-1, but from 13.73 g (0.057 mol) of 2-Cyclohexyl-2-fur-2-yl-2-hydroxyacetic acid methyl ester (Intermediate I-11) dissolved in 350 ml of toluene, 8.6 g (0.067 mol) of (3R)-3-hydroxy-1-azabicyclo[2.2.2]octane and 1.37 g (0.0342 mol) of HNa (60% dispersion in mineral oil). The oil obtained (10.33 g) was purified by chromatography on silica gel eluting with chloroform/methanol/ammonia 97:3:0.3. Appropriate fractions were combined and evaporated to obtain the two diastereomers: I-4a and I-4b.

Provenance & Evidence