Reaktion #713941

Reaktionsgleichung

3-(6-chloropyridin-3-yl)-azetidine-1-carboxylic acid tert-butyl ester

benzophenone imine

Xantphos

cesium carbonate

→

title compound

Ausbeute 70.9%

3-[6-(Benzhydrylideneamino)-pyridin-3-yl]-azetidine-1-carboxylic acid tert-butyl ester

Ausbeute 70.9%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas de-gassed
2. 2
   Sonstigepurged with nitrogen
3. 3
   Temperaturto cool to room temperature
4. 4
   Sonstigebefore being partitioned between ethyl acetate and water
5. 5
   SonstigeThe layers were separated
6. 6
   Waschenthe organic layer was washed with brine
7. 7
   Trocknendried over anhydrous sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    SonstigeThe residue was purified by silica gel flash chromatography (30-40% ethyl acetate in cyclohexane)

Vorschrift

A mixture of 3-(6-chloropyridin-3-yl)-azetidine-1-carboxylic acid tert-butyl ester (274 mg, 1.0 mmol), benzophenone imine (0.2 mL, 1.2 mmol), Pd2(dba)3 (22 mg, 0.025 mmol), Xantphos (58 mg, 0.10 mmol) and cesium carbonate (652 mg, 2.0 mmol) in dioxane (10 mL) was de-gassed and purged with nitrogen and the reaction mixture was heated at 80° C. in a sealed vial overnight. The resultant mixture was allowed to cool to room temperature, before being partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (30-40% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (293 mg, 70% yield). LCMS (Method C): RT=3.31 min, m/z: 269 [M+H+].

Quelle