Benzenesulfonyl chloride → (R)-quinuclidin-3-yl 2-phenyl-2-(phenylsulfonamido)acetate

Participants

Reaction Steps

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (0.67 g, 2.01 mmol) in DCM (25 ml), were sequentially added triethylamine (0.84 ml, 6.04 mmol) and benzenesulfonyl chloride (0.31 ml, 2.42 mmol). The reaction was stirred at RT for 4 hours, and then the solvent was evaporated. The residue was taken up with EtOAc, and washed with water and brine, dried over Na2SO4 and evaporated to obtain (R)-quinuclidin-3-yl 2-phenyl-2-(phenylsulfonamido)acetate (370 mg; 46% yield).

Provenance & Evidence