反応 #88179

反応方程式

water

Triethylamine

(R)-3-(2-ethoxy-phenoxy)-piperidine

ethyl 6-chloronicotinate

→

ethyl (R)-6-(3-(2-ethoxyphenoxy)piperidin-1-yl)nicotinate

収率 60.9%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度The mixture was cooled to ambient temperature
2. 2
   抽出the mixture was extracted with ethyl acetate (3×200 mL)
3. 3
   洗浄The combined organic layers were washed sequentially with water (100 mL) and brine (100 mL)
4. 4
   乾燥were dried over sodium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他The crude material was purified by column chromatography (13% ethyl acetate-hexanes)

実験手順

Triethylamine (8.1 mL, 80 mmol) was added to a stirred solution of (R)-3-(2-ethoxy-phenoxy)-piperidine (10 g, 39 mmol) and ethyl 6-chloronicotinate (7.2 ml, 39 mmol) in acetonitrile (100 mL) at 0° C. The reaction mixture was heated at 90° C. for 16 h. The mixture was cooled to ambient temperature, water (150 mL) was added, and the mixture was extracted with ethyl acetate (3×200 mL). The combined organic layers were washed sequentially with water (100 mL) and brine (100 mL), then were dried over sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography (13% ethyl acetate-hexanes) to afford ethyl (R)-6-(3-(2-ethoxyphenoxy)piperidin-1-yl)nicotinate (8.8 g). MS (ES+) 371.0 (M+H).

出典