반응 #2442710

반응 방정식

(3S,4S)-benzyl 3-(tert-butoxycarbonylamino)-4-cyclohexylpiperidine-1-carboxylate

NaOH

→

(3S,4S)-benzyl 3-amino-4-cyclohexylpiperidine-1-carboxylate

수율 86.5%

용매

HCl acetonitrile

반응 조건

후처리

1. 1
   기타The acetonitrile was removed under vacuum
2. 2
   추출The aqueous residue was extracted with CH2Cl2 (3×20 mL)
3. 3
   세척The combined organic layers were washed with brine (10 mL)
4. 4
   건조dried over Na2SO4
5. 5
   농축Concentration

실험 절차

(3S,4S)-benzyl 3-(tert-butoxycarbonylamino)-4-cyclohexylpiperidine-1-carboxylate (35 mg, 0.084 mmol) was dissolved in 1:1 2N aq HCl/acetonitrile (8 mL) and stirred overnight at rt. LC-MS showed the reaction was complete. The reaction mixture was basified with 5% aq NaOH solution to about pH=9. The acetonitrile was removed under vacuum. The aqueous residue was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine (10 mL) and dried over Na2SO4. Concentration afforded (3S,4S)-benzyl 3-amino-4-cyclohexylpiperidine-1-carboxylate (23 mg, 86% yield). The crude product was used in the next step without further purification. LC-MS (3 min) tR=1.31 min., m/z 317 (M+1).

출처