反応 #1528418

反応方程式

tert-butyl 4-cyanopiperidine-1-carboxylate

2-(chloromethyl)pyridine

potassium bis(trimethylsilyl)amide

→

desired product

Tert-butyl 4-cyano-4-(pyridine-2-ylmethyl)piperidine-1-carboxylate

溶媒

toluene

brine

反応条件

後処理

1. 1
   温度cooled in an ice bath
2. 2
   抽出extracted with EtOAc (3×30 ml)
3. 3
   洗浄The combined organic extracts were washed with brine (30 ml)
4. 4
   乾燥dried over MgSO4
5. 5
   ろ過filtered
6. 6
   その他evaporated
7. 7
   その他to give a orange oil
8. 8
   その他The crude product was chromatographed on silica
9. 9
   洗浄eluted with 50% EtOAc in isohexane

実験手順

To a stirred suspension of tert-butyl 4-cyanopiperidine-1-carboxylate (500 mg; 2.38 mmol) and 2-(chloromethyl)pyridine (334 mg; 2.62 mmol) in toluene (3.6 ml) cooled in an ice bath was added a solution of potassium bis(trimethylsilyl)amide (0.5 M in toluene; 5.7 ml; 2.86 mmol) over 10 minutes. The reaction mixture was allowed to warm to ambient temperature with stirring for 1.5 hours. The reaction was poured into brine (25 ml) and extracted with EtOAc (3×30 ml). The combined organic extracts were washed with brine (30 ml), dried over MgSO4, filtered and evaporated to give a orange oil. The crude product was chromatographed on silica eluted with 50% EtOAc in isohexane to give the desired product a colourless oil. (375 mg)

出典