تفاعل #420146

معادلة التفاعل

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

2,6-dinitrobenzonitrile

NaH

→

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

المردود 91.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةUpon completion, the reaction was cooled to 0° C.
2. 2
   أخرىquenched with water
3. 3
   استخلاصThe mixture was extracted with ethyl acetate
4. 4
   تجفيفdried over anhydrous Na2SO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىThe residue was recrystallized from ethyl acetate/hexanes

الإجراء التجريبي

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).

المصدر