反应详情

A 1.6 N solution of BuLi in hexane (730 μA, 1.16 mmol) was added dropwise to a solution of 3-ethynyl-3-fluoroquinuclidine 57 (162 mg, 1.06 mmol) in THF (5 ml) at 0° C. After stirring for 30 minutes, cyclohexyl(phenyl)methanone (207 mg, 1.16 mmol) in THF (1 ml) was added slowly. After 30 minutes, the reaction was quenched by the addition of saturated aqueous NH4Cl solution and diluted with AcOEt. The organic phase was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by chromatography over silica gel (CH2Cl2/MeOH 97.5/2.5) and 1-cyclohexyl-3-(3-fluoro-1-azabicyclo[2.2.2]oct-3-yl)-1-phenylprop-2-yn-1-ol 111 was obtained as colorless foam (mixture of diastereomers, 30 mg, 8%).

1. waitAfter 30 minutes
2. customthe reaction was quenched by the addition of saturated aqueous NH4Cl solution
3. additiondiluted with AcOEt
4. washThe organic phase was washed with brine
5. dry with materialdried over Na2SO4
6. customevaporated
7. customThe residue was purified by chromatography over silica gel (CH2Cl2/MeOH 97.5/2.5)