Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(benzyloxycarbonylamino)-2-phenylacetate

Participants

Reaction Steps

To a solution of 2-(benzyloxycarbonylamino)-2-phenylacetic acid (I28) (855 mg, 3.00 mmol) in THF (20 ml), were added (R)-quinuclidin-3-ol (457 mg, 3.60 mmol), N,N′-methanediylidenedicyclohexanamine (742 mg, 3.60 mmol) and 1H-benzo[d][1,2,3]triazol-1-ol (486 mg, 3.60 mmol). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The residue was taken up with DCM, the insoluble solid was filtered off, and the clear solution was washed twice with Na2CO3 and brine, dried over Na2SO4 and evaporated. The resulting crude is purified by silica gel flash chromatography (DCM/MeOH=9/1) to obtain (R)-quinuclidin-3-yl 2-(benzyloxy-carbonylamino)-2-phenylacetate (925 mg; 78% yield).

Provenance & Evidence