Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(methyl(phenyl)amino)acetate

Participants

Reaction Steps

A mixture of 2-(benzo[b]thiophen-3-yl)-2-(methyl(phenyl)amino)acetic acid (I34) (351 mg, 1.18 mmol), (R)-quinuclidin-3-ol (180 mg, 1.42 mmol), DCC (292 mg, 1.42 mmol), and HOBT (217 mg, 1.42 mmol) in dry THF (20 ml) was stirred at room temperature overnight. The solvent was evaporated, and the crude product was portioned between EtOAc and 2M K2CO3. The organic phase was washed with 2M K2CO3 and brine, dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (MeCN/MeOH=8/2+0.2% NH4OH) to obtain (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(methyl(phenyl)amino)acetate (224 mg, 46.7% yield).

Provenance & Evidence