반응 #420146

반응 방정식

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

2,6-dinitrobenzonitrile

NaH

→

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

수율 91.0%

용매

THF

반응 조건

후처리

1. 1
   온도Upon completion, the reaction was cooled to 0° C.
2. 2
   기타quenched with water
3. 3
   추출The mixture was extracted with ethyl acetate
4. 4
   건조dried over anhydrous Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was recrystallized from ethyl acetate/hexanes

실험 절차

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).

출처