Imidazole → HCID 178511533, compound

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to an ice-cold solution of trans-4-benzyloxycarbonylaminocyclohexane-methanol (292 mg, 1.11 mmol), triphenylphoshine on polystyrene (3.52 mmol) and imidazole (107 mg, 1.55 mmol) in dry CH2Cl2 (40 mL) was added iodine (455 mg, 1.77 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 (0.34 mL, 4.09 mmol) and K2CO3 (566 mg, 4.09 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 (147 mg) in MeOH (10 mL) under a H2 atmosphere. The title compound was obtained as a colorless oil. LC-MS-conditions 07d: tR=0.97 min; [M+H]+=183.37.

1. filtrationThe mixture was then filtered
2. washsuccessively washed with 10% aq. Na2SO3 and brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. dissolutionThe crude iodide was redissolved in CH3CN (15 mL)
7. temperatureThe reaction mixture was refluxed until completion of the reaction
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe amine was purified by FC (hept-EA, 1:0->1:1)
11. customthe Cbz group was removed by treatment with 10% Pd/C (147 mg) in MeOH (10 mL) under a H2 atmosphere

ORD record

ord-d1c492ca251f4f048adf3869a4bdd8db

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563714B2