反应详情

To a solution of (R)-(4-fluoro-phenylamino)-phenyl-acetic acid (I253) (420 mg, 1.71 mmol) in dry THF (40 mL), are sequentially added (S)-quinuclidin-3-ol (218 mg, 1.71 mmol), DEAD (407 ul, 2.57 mmol) and triphenylphosphine (674 mg, 2.57 mmol). The reaction is refluxed for 30 minutes under N2 flowstream and then the solvent is evaporated. The residue is partitioned between water and EtOAc, the organic layer is separated, dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is purified by flash chromatography (DCM/MeOH=95/5) to obtain the title compound as a pale yellow oil (480 mg, 79% yield).

1. temperatureThe reaction is refluxed for 30 minutes under N2 flowstream
2. customthe solvent is evaporated
3. customThe residue is partitioned between water and EtOAc
4. customthe organic layer is separated
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customevaporated to dryness
8. customThe resulting crude is purified by flash chromatography (DCM/MeOH=95/5)