Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(methyl(phenyl)amino)-2-phenylacetate

Participants

Reaction Steps

2-(Methyl(phenyl)amino)-2-phenylacetic acid (I35) (2.20 g, 9.12 mmol) was dissolved in THF (25 ml), and (R)-quinuclidin-3-ol (1.28 g, 10.0 mmol) was added. To the resulting solution, HOBt (1.23 g, 9.12 mmol) and DCC (1.88 g, 9.12 mmol) were added, and the mixture was stirred at room temperature for three days. THF was removed under vacuum and the residue was portioned between H2O and EtOAc. The organic phase was washed with a saturated aqueous Na2CO3 solution, dried over Na2SO4 and evaporated to dryness. The crude was purified by flash chromatography (EtOAc to EtOAc/MeOH=75/25) to afford (R)-quinuclidin-3-yl 2-(methyl(phenyl)amino)-2-phenylacetate (2.2 g, 68.8% yield, mixture of diastereomers).

Provenance & Evidence