反应详情

温度

2.5 °C

In a 50 mL three-necked round bottom flask (flame dried) charged with a magnetic stirrer and under inert atmosphere to 1080 mg polymer bound triphenylphosphine (3 mmol/g) in 10 mL THF was added 502 mg (2.18 mmol) di-tert-butyl azodicarboxylate in 5 mL THF and 265 mg (2.04 mmol) 5-chloro-2-hydroxypyridine in 10 mL THF at 0-5° C. The brownish suspension was stirred for 20 min at 0-5° C. 450 mg (1.36 mmol) (RS)-1-[(3SR,4SR)-1-benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-ethanol in 5 mL THF was added and the ice bath was removed and the reaction was stirred for 63 h at room temperature. The suspension was filtered over a Dicalit-filter. The filtrate was concentrated under vacuum and the residue was purified by chromatography over silica eluting with a gradient formed from i-propanol and heptane to yield after evaporation of the product containing fractions 480 mg (80%) of the title compound as yellow viscous oil. MS (m/e): 441.2 [(M+H)+].

1. temperatureIn a 50 mL three-necked round bottom flask (flame dried)
2. customthe ice bath was removed
3. stirringthe reaction was stirred for 63 h at room temperature
4. filtrationThe suspension was filtered over a Dicalit-filter
5. concentrationThe filtrate was concentrated under vacuum
6. customthe residue was purified by chromatography over silica eluting with a gradient
7. customformed from i-propanol and heptane
8. customto yield
9. customafter evaporation of the product
10. additioncontaining fractions 480 mg (80%) of the title compound as yellow viscous oil