Dicyclohexylcarbodiimide → HCID 58557008, compound

Participants

Reaction Steps

A mixture of 2-(benzo[b]thiophen-3-yl)-2-(3-methoxyphenylamino)acetic acid (I46) (1.02 g, 3.25 mmol), (R)-quinuclidin-3-ol (496 mg, 3.90 mmol), DCC (805 mg, 3.90 mmol), and HOBT (597 mg, 3.90 mmol) in dry THF (30 ml) was stirred at r.t. overnight. THF was evaporated, and the crude product was taken up with EtOAc and washed twice with 1M K2CO3 and then with brine. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (DCM/MeOH=98/2 to 95/5) to obtain (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(3-methoxyphenylamino)acetate (213 mg, 15.5% yield over two steps).

Provenance & Evidence