Dicyclohexylcarbodiimide → HCID 67607091, compound

Participants

Reaction Steps

To a solution of 2-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)acetic acid (I46) (2.17 g, 7.58 mmol) in dry THF (70 ml), were added N,N′-methanediylidenedicyclohexanamine (1.88 g, 9.10 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (1.23 g, 9.10 mmol), and (R)-quinuclidin-3-ol (1.16 g, 9.10 mmol). The reaction was stirred at RT for 15 hours, and the solvent was evaporated. The residue was taken up with DCM, the insoluble solid was filtered off, and the organic solution was washed twice with aq. Na2CO3 and then brine, dried over Na2SO4 and evaporated. The crude was purified by flash chromatography (EtOAc/MeOH=8/2 to 85/15) to obtain (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)acetate (1.33 g; 44% yield).

Provenance & Evidence