反应详情

2-Phenyl-2-(piperidin-1-yl)acetic acid hydrochloride (0.87 g, 3.40 mmol) was suspended in dry THF (34.0 ml) and, while stirring at room temperature, DCC (1.40 g, 6.80 mmol), HOBT (1.04 g, 6.80 mmol) and (R)-quinuclidin-3-ol (1.30 g, 10.21 mmol) were sequentially added. The white suspension was stirred at the same temperature overnight (UPLC-MS: complete conversion). THF was evaporated and the residue was taken up with EtOAc (30 ml) and washed with water (20 ml) and then with a sat. NaHCO3 (20 ml). The organic phase was dried over Na2SO4, filtered was evaporated. The crude was purified by flash chromatography (DCM/MeOH/NH4OH=98/2/0.2 to 97/3/0.3) to obtain (R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate (40 mg, 40% yield) as a colorless oil.

1. stirringThe white suspension was stirred at the same temperature overnight (UPLC-MS: complete conversion)
2. customTHF was evaporated
3. washwashed with water (20 ml)
4. dry with materialThe organic phase was dried over Na2SO4
5. filtrationfiltered
6. customwas evaporated
7. customThe crude was purified by flash chromatography (DCM/MeOH/NH4OH=98/2/0.2 to 97/3/0.3)