Potassium Carbonate → HCID 178486052, compound

Participants

Reaction Conditions

Reaction Steps

suspension of 6-Hydroxy-2H-isoquinolin-1-one (410 mg, 2.52 mmol) and potassium carbonate (420 mg, 3.03 mmol) in DMF (7 ml) was heated to 110° C. and a solution of methanesulfonic acid cis-4-(tert-butoxycarbonylmethylamino)cyclohexyl ester (930 mg, 3.03 mmol) in DMF (3 ml) was added dropwise. Heating was continued at 110° C. for 16 hours and the solvent removed in vacuo. The residue was taken up in chloroform/isopropanol (3:1) and washed with aqueous sodium hydrogen carbonate. The organics were collected through a hydrophobic frit and concentrated to afford crude product. The residue was purified by flash chromatography on silica (eluent: dichloromethane followed by 2M ammonia in methanol) to give trans-methyl[4-(1-oxo-1,2-dihydroisoquinolin-6-yloxy)cyclohexyl]carbamic acid tert-butyl ester (400 mg, 42%), EI-MS: m/z=373.1 [M+H]+.

Provenance & Evidence