Dicyclohexylcarbodiimide → HCID 67606929, compound

Participants

Reaction Steps

A mixture of (S)-3-(4-(benzyloxy)phenyl)-2-(tert-butoxycarbonyl-amino)propanoic acid (500 mg, 1.35 mmol), DCC (333 mg, 1.61 mmol) and HOBT (247 mg, 1.61 mmol) in dry THF (10 ml) was stirred at RT under nitrogen atmosphere for 1 hour. (R)-quinuclidin-3-ol (205 mg, 1.61 mmol) was added, and the reaction was stirred for 16 hours. The solvent was evaporated, and the residue was portioned between saturated NaHCO3 and EtOAc. The organic phase was washed with brine, dried over Na2SO4 filtered and evaporated to dryness. The residue was triturated with Et2O (30 ml), and the insoluble material was removed by filtration. The solution was evaporated to obtain (S)—((R)-quinuclidin-3-yl) 3-(4-(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)-propanoate (590 mg, 91% yield).

Provenance & Evidence