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

Participants

Reaction Steps

A mixture of 2-(tert-butoxycarbonylamino)-2-phenylacetic acid (I3) (2.00 g, 7.96 mmol), (R)-quinuclidin-3-ol (1.21 g, 9.55 mmol), HOBt (1.46 g, 9.55 mmol), and DCC (1.97 g, 9.55 mmol) in dry THF (70 ml) was stirred at RT overnight. Then THF was evaporated and the crude was taken up with DCM and washed twice with 2M K2CO3 and brine. The organic phase was dried over Na2SO4, filtered, and evaporated to dryness. The crude was purified by flash chromatography (DCM/MeOH=95/5) to get (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate (1.68 g; 58.5% yield).

Provenance & Evidence