反应详情

温度

15 °C

136 g (<528 mmol) 4-[1-tert-butoxycarbonylpiperidin-4-yl)-butan-1-ol (crude product), 135.3 g (516 mmol) Triphenylphosphine and 75.9 g (516 mmol) phthalimide are suspended in 1800 ml THF and 89.9 g (516 mmol) azodicarboxylic acid diethyl ester are added dropwise within three hours under protective atmosphere and light cooling (to ca. 15° C.). The mixture is left to stand at RT overnight without further cooling. Subsequently, the solvent is removed under vacuum and the oily residue is dissolved in 500 ml acetic acid ethyl ester and held at 0° C. overnight. The sedimented precipitate is filtered and discarded. The solution is concentrated under vacuum and the oily residue is chromatographically purified over silica gel with CHCl3 and crystallized from 200 ml isopropanol after drawing off the solvent. Colorless crystals remain with a MP of 100–102° C.; yield: 108.5 g (57%).

1. waitThe mixture is left
2. customSubsequently, the solvent is removed under vacuum
3. dissolutionthe oily residue is dissolved in 500 ml acetic acid ethyl ester
4. waitheld at 0° C. overnight
5. filtrationThe sedimented precipitate is filtered
6. concentrationThe solution is concentrated under vacuum
7. customthe oily residue is chromatographically purified over silica gel with CHCl3
8. customcrystallized from 200 ml isopropanol