Dicyclohexylcarbodiimide → HCID 86688891, compound

Participants

Reaction Steps

PS-DCC (loading: 1.25 mmol/g; 0.99 g, 1.24 mmol) was suspended in dry THF (12 ml). HOBT (0.19 g, 1.24 mmol), 2-phenyl-2-(pyrrolidin-1-yl)acetic acid hydrochloride (0.15 g, 0.62 mmol) and (R)-quinuclidin-3-ol (0.24 g, 1.86 mmol) were sequentially added. The mixture was shaken overnight and then PS-DCC was filtered washing with EtOAc and THF. The solution was evaporated and the residue was dissolved in EtOAc (30 ml) and washed with water (15 ml) and with a sat. NaHCO3 (20 ml). The organic phase was dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography (DCM/MeOH=92/8 to 85/15) to obtain (R)-quinuclidin-3-yl 2-phenyl-2-(pyrrolidin-1-yl)acetate (53 mg, 27.2% yield) as a colorless oil.

Provenance & Evidence