Dicyclohexylcarbodiimide → HCID 58557024, compound

Participants

Reaction Steps

A mixture of 2-(benzo[b]thiophen-3-yl)-2-(2-ethylphenylamino)acetic acid (I43) (875 mg, 2.81 mmol), HOBT (430 mg, 2.81 mmol), and DCC (1.16 g, 5.62 mmol) in THF (28 ml) was stirred at r.t. for 30 minutes. Then (R)-quinuclidin-3-ol (715 mg, 5.62 mmol) was added, and the reaction mixture was stirred at r.t. overnight. The solvent was evaporated, and the crude product was partitioned between EtOAc and sat. Na2CO3. The organic phase was dried over sodium sulphate, filtered and evaporated to dryness. The crude was purified by flash chromatography (EtOAc/MeOH=3/1) to collect (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(2-ethylphenylamino)acetate (86 mg, 7.3% yield over two steps)

Provenance & Evidence