反应 #420146

反应方程式

(R)-tert-butyl-2-(hydroxymethyl)piperidine-1-carboxylate

2,6-dinitrobenzonitrile

NaH

→

(R)-tert-butyl-2-((2-cyano-3-nitrophenoxy)methyl)piperidine-1-carboxylate

收率 91.0%

溶剂

THF

反应条件

后处理

1. 1
   温度Upon completion, the reaction was cooled to 0° C.
2. 2
   其他quenched with water
3. 3
   萃取The mixture was extracted with ethyl acetate
4. 4
   干燥dried over anhydrous Na2SO4
5. 5
   过滤filtered
6. 6
   浓缩concentrated
7. 7
   其他The residue was recrystallized from ethyl acetate/hexanes

实验过程

To a solution of (R)-tert-butyl-2-(hydroxymethyl)piperidine-1-carboxylate (Example 15f, 7.10 g, 33.0 mmol) and 2,6-dinitrobenzonitrile (6.37 g, 33.0 mmol) in THF (142 mL) cooled to -78° C., was added NaH (60% dispersion in oil, 1.45 g, 36.3 mmol). The reaction was allowed to warm to room temperature and stirring was continued for 18 hours. Upon completion, the reaction was cooled to 0° C. and quenched with water. The mixture was extracted with ethyl acetate, and the organic extracts were combined and dried over anhydrous Na2SO4, filtered, and concentrated. The residue was recrystallized from ethyl acetate/hexanes to afford (R)-tert-butyl-2-((2-cyano-3-nitrophenoxy)methyl)piperidine-1-carboxylate (10.8 g, 91%) as a yellow solid. MS 282 (MH+-boc).

来源