Imidazole → HCID 178511532, compound

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to an ice-cold solution of cis-4-benzyloxycarbonylaminocyclohexane-methanol (267 mg, 1.01 mmol), triphenylphoshine on polystyrene (3.20 mmol) and imidazole (97 mg, 1.42 mmol) in dry CH2Cl2 (40 mL) was added iodine (416 mg, 1.62 mmol). The reaction mixture was warmed to rt and stirred at this temperature until completion of the reaction. The mixture was then filtered, successively washed with 10% aq. Na2SO3 and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude iodide was redissolved in CH3CN (15 mL) and treated with pyrrolidine (0.32 mL, 3.86 mmol) and K2CO3 (533 mg, 3.86 mmol). The reaction mixture was refluxed until completion of the reaction, filtered and concentrated under reduced pressure. The amine was purified by FC (hept-EA, 1:0->1:1) and then the Cbz group was removed by treatment with 10% Pd/C (116 mg) in EtOH (20 mL) under a H2 atmosphere. The title compound was obtained as a white solid. LC-MS-conditions 04: tR=0.99 min; [M+H]+=183.35.

Provenance & Evidence