1,1'-Carbonyldiimidazole → HCID 57619816, compound

Participants

Reaction Steps

A solution of tert-butyl 4-[4-[[(1S,2S)-2-aminocyclohexyl]amino]-1-piperidyl]-4-methyl-piperidine-1-carboxylate (10.0 mmol) in acetonitrile (30 mL) was added with 1,1′-carbonyldiimidazole (1.95 g, 12.0 mmol) and stirred at room temperature for 12 h. Concentrated in vacuo and was added with water (20 mL) and dichloromethane (100 mL), phases were separated and the aqueous phase was extracted with dichloromethane (2×50 mL). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified with preparative LC/MS (high pH) to provide the title compound as white solid (1.18 g, 28% over two steps). 1H NMR (400 MHz, METHANOL-D4) δ ppm 0.95 (s, 3H), 1.31-1.40 (m, 4H), 1.42 (s, 9H), 1.44-1.48 (m, 2H), 1.52-1.63 (m, 1H), 1.64-1.89 (m, 8H), 1.93-1.99 (m, 1H), 2.08-2.21 (m, 2H), 2.25-2.32 (m, 1H), 2.89-3.10 (m, 4H), 3.28-3.36 (m, 1H), 3.42-3.53 (m, 2H), 3.54-3.65 (m, 1H). MS (M+1): 421.3.

Provenance & Evidence