反应详情

To a stirred solution of N-Cbz-L-prolinal (6.3 g, 27 mmol, from step 24d above) in 30 mL of benzene was added 9.42 g (29.6 mmol) of 1-triphenylphosphoranylidene-2-propanone (Aldrich) at room temperature. The reaction mixture was heated to reflux for 4 hr. The benzene was removed under vacuum, and the residue was dissolved in ether and cooled for 16 hr. The phosphine oxide by product was removed by filtration, and the solution was further purified by column chromatography on silica gel, eluting with 20% ethyl acetate in hexanes, to afford 4.4 g of the title product (69% yield).

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 4 hr
3. customThe benzene was removed under vacuum
4. dissolutionthe residue was dissolved in ether
5. temperaturecooled for 16 hr
6. customThe phosphine oxide by product was removed by filtration
7. customthe solution was further purified by column chromatography on silica gel
8. washeluting with 20% ethyl acetate in hexanes