Triphenylphosphine → (S)-quinuclidin-3-yl 2-phenyl-2-(phenylamino)acetate

Beteiligte Stoffe

Reaktionsschritte

To a solution of 2-phenyl-2-(phenylamino)acetic acid (I1) (500 mg, 2.20 mmol), (R)-quinuclidin-3-ol (280 mg, 2.20 mmol) and triphenylphosphine (577 mg, 2.20 mmol) in dry THF (7 mL) cooled at 0° C., is added (E)-diethyl diazene-1,2-dicarboxylate (0.35 mL, 2.20 mmol) and the reaction is stirred for 2 hours at RT. The solvent is removed under vacuum and the residue is taken up with EtOAc, washed with 5% NaHCO3 and brine, dried over Na2SO4 and evaporated to dryness. The resulting yellow oil is purified by flash chromatography (EtOAc/MeOH/NH4OH=90/10/0.1 to 70/30/0.1) to obtain desired product as a white powder (78.0 mg, 10% yield, mixture of diasteroisomer).

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