Dicyclohexylcarbodiimide → HCID 118135599, compound

Participants

Reaction Steps

A solution of 2-(((benzyloxy)carbonyl)amino)-2-(3-(benzyloxy)phenyl)acetic acid (2.1 g, 5.3 mmol), N,N′-dicyclohexylcarbodiimide (1.20 g, 5.83 mmol), 1-hydroxybenzotriazole hydrate (787 mg, 5.83 mmol) and (R)-quinuclidin-3-ol (1.70 g, 13.5 mmol) in dry tetrahydrofuran (27 mL) was stirred at room temperature for 18 h. Additional (R)-quinuclidin-3-ol (1.70 g, 13.5 mmol) was then added to the mixture and stirred for 4 days. The white slurry was then filtered through a pad of Celite®, rinsed with ethyl acetate (100 mL) and the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (100 mL) and saturated sodium carbonate (50 mL). The layers were separated and the aqueous phase back-extracted with ethyl acetate (2×50 mL). The combined organic fractions were dried over magnesium sulfate, filtered and the solvent was removed in vacuo. The residue was purified by silica gel column chromatography, eluting with 0-40% ethyl acetate/10% methanolic ammonia solution in ethyl acetate to afford the title compound (1.5 g, 56%) as a clear thick oil.

Provenance & Evidence