Cyclohexanone → HCID 70979874, compound

Participants

Reaction Steps

To a solution of (6-cyano-5-nitro-pyridin-2-yl)-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester Example 20 (Step 2) (1.10 g, 2.65 mmol, 1 equiv) and cyclohexanone (320 μL, 3.20 mmol, 1.2 equiv) in THF (10 mL) and acetic acid (20 mL), was added Pd/C (10%, 200 mg) and the reaction mixture was hydrogenated overnight. The catalyst was removed by filtration and the filtrate evaporated to give an oil. The oil was dissolved in DCE (15 mL) and treated with cyclohexanone (100 μL, 1.0 mmol) followed by sodium triacetoxyborohydride (954 mg, 4.5 mmol, 1.7 equiv). The reaction mixture was stirred at ambient temperature for 2 h, saturated NaHCO3 was added and the product was extracted with dichloromethane. The organic phase was dried (MgSO4), filtered and the solvent evaporated. The crude material was purified by column chromatography (SiO2, eluted with dichloromethane—MeOH 0-10%) to afford (5-amino-6-cyclohexylaminomethyl-pyridin-2-yl)-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (390 mg). MS: [M+H]+=471.

Provenance & Evidence