Reaktion #657976

Reaktionsgleichung

Potassium tert-butoxide

1-Boc-4-hydroxypiperidine

4-Chloro-2,3-dimethylpyridine

→

title compound

tert-butyl 4-[(2,3-dimethylpyridin-4-yl)oxy]piperidine-1-carboxylate

ammonia

Lösungsmittel

dimethylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at 50° C. for 18 hours
2. 2
   SonstigeThe mixture was partitioned between ethyl acetate and water
3. 3
   Sonstigethe organic layer was separated
4. 4
   Waschenwashed with sodium hydrogen carbonate solution and brine
5. 5
   TrocknenThe organic solution was then dried over magnesium sulfate
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigethe residue was purified by column chromatography on silica gel
8. 8
   Wascheneluting with dichloromethane

Vorschrift

Potassium tert-butoxide (4.70 g, 42 mmol) was added to a solution of 1-Boc-4-hydroxypiperidine (4.05 g, 20.1 mmol) in dimethylsulfoxide (20 mL) and the mixture was stirred at room temperature for 1 hour. 4-Chloro-2,3-dimethylpyridine (3.58 g, 20.1 mmol) was then added and the reaction mixture was stirred at 50° C. for 18 hours. The mixture was partitioned between ethyl acetate and water, and the organic layer was separated and washed with sodium hydrogen carbonate solution and brine. The organic solution was then dried over magnesium sulfate concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 100:0:0 to 94:6:0.6, to afford the title compound as an oil in 39% yield, 2.4 g.

Quelle