反应详情

温度

0 °C

A solution of 4,4-Diethoxy-1-((S)1-phenyl-ethyl)-(R)-2-hydroxymethyl-piperidine (65.35 g, 0.213 mmol), triphenylphosphine (61.3 g, 0.234 mol) and phthalimide (34.4 g, 0.234 mol), in tetrahydrofuran (700 ml) cooled to 0° C. was added diethyl azodicarboxylate over the course of 1.5 hour. The reaction mixture was stirred at 0° C. for another 2 hours before the solvent was removed in vacuo. The residue was dissolved in hot heptane-toluene (3:2) (650 ml) before it was cooled on an ice bath. The precipitate consisting of triphenyl phosphine oxide was filtered off and washed with heptane. The filtrate was concentrated in vacuo and the residue subjected to column chromatography using a mixture of toluene-ethyl acetate-heptane (3:1:3) as eluent. The solvent was evaporated in vacuo whereupon a viscous oil was obtained. Upon addition of light petrol ether the product crystallized to give 67.4 g (73%) of the title compound as a solid.

1. customwas removed in vacuo
2. dissolutionThe residue was dissolved in hot heptane-toluene (3:2) (650 ml) before it
3. temperaturewas cooled on an ice bath
4. filtrationwas filtered off
5. washwashed with heptane
6. concentrationThe filtrate was concentrated in vacuo
7. additiona mixture of toluene-ethyl acetate-heptane (3:1:3) as eluent
8. customThe solvent was evaporated in vacuo whereupon a viscous oil
9. customwas obtained
10. customcrystallized