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

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Reaction Steps

(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).

Provenance & Evidence