Dicyclohexylcarbodiimide → HCID 58556901, compound

Participants

Reaction Steps

Polymer-Supported DiCyclohexylCarbodiimide (PS-DCC) (972 mg, 1.29 mmol, loading: 1.33 mmol/g) was suspended in dry tetrahydrofuran (10 ml). 2-(3-fluorophenyl)-2-(3,4,5-trifluorophenylamino)acetic acid hydrochloride (I42) (217 mg, 0.65 mmol), HOBT (198 mg, 1.29 mmol), and (R)-quinuclidin-3-ol (247 mg, 1.94 mmol) were added, and the mixture was shaken at r.t. for 16 hours. PS-DCC was filtered off, the filtrate was evaporated and the residue was dissolved in EtOAc and washed with NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and evaporated. The resulting crude compound was purified by filtration through a pad of silica-gel eluting with DCM/MeOH=93/7. The resulting white foam was dissolved in DCM and passed through an Isolute PE-AX cartridge (5 g, 0.6 mmol/g, DCM/MeOH=9/1) to obtain (R)-quinuclidin-3-yl 2-(3-fluorophenyl)-2-(3,4,5-trifluorophenylamino)acetate (264 mg, 32% yield).

Provenance & Evidence