Dicyclohexylcarbodiimide → (S)-((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-3-phenylpropanoate

Participants

Reaction Steps

A mixture of (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (500 mg, 1.88 mmol), DCC (467 mg, 2.26 mmol), and HOBT (346 mg, 2.26 mmol) in dry THF (15 ml) was stirred for 30 minutes at RT. Then (R)-quinuclidin-3-ol (288 mg, 2.26 mmol) was added portionwise and the reaction was stirred at RT for 16 hours. The solvent was evaporated, the residue was dissolved in EtOAc, and the insoluble was removed by filtration. The organic phase was washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered and evaporated to obtain (S)—((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-3-phenylpropanoate (600 mg, 85% yield).

Provenance & Evidence