1,2-Diaminocyclohexane, (+)- → ethyl 4-[4-[[(1S,2S)-2-aminocyclohexyl]amino]-1-piperidyl]-4-methyl-piperidine-1-carboxylate

Participants

Reaction Steps

To a solution ethyl 4-methyl-4-(4-oxo-1-piperidyl)piperidine-1-carboxylate (336 mg, 1.25 mmol) and (1S,2S)-cyclohexane-1,2-diamine (286 mg, 0.5 mmol) in dichloromethane (10 mL) was added sodium triacetoxyborohydride (398 mg, 1.88 mmol) and stirred at room temperature for 12 h. Saturated NaHCO3 (5 mL) was added, the phases were separated and the aqueous phase was extracted with dichloromethane (2×10 mL). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by passing through a short silica gel pad (5-10% MeOH in dichloromethane) to afford the title compound (87 mg, 19%). MS (M+1): 367.31.

Provenance & Evidence