Coumaranone → HCID 86666753, compound

Participants

Reaction Steps

To a stirred solution of 80 mg (0.47 mmol) of the title compound from Step C and 87 mg (0.47 mmol) tert-butyl 1-piperazine-carboxylate in 20 ml THF was added 39 mg (0.47 mmol) sodium bicarbonate and 0.27 ml (0.93 mmol) of titanium(IV) isopropoxide. The reaction was stirred at RT for 30 min, and was heated at 70° C. for 4 h. The reaction was cooled down to ambient temperature and 200 mg (0.93 mmol) of sodium triacetoxyborohydride was added into the mixture. The reaction was continued by stirring at ambient temperature overnight. The reaction was quenched with methanol and concentrated. The reaction was partitioned between ethyl acetate and water, the organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by reverse-phase HPLC (TMC Pro-Pac C18; 10-100% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient) to give the intermediate with double bond. To the above intermediate was added 20 ml methanol and 5 mg of 10% Palladium on carbon. Hydrogenation was carried out under the hydrogen gas balloon for 4 hr. The reaction mixture was filtered and the filtrate was concentrated to afford the title compound. LC/MS: (M-56): 249.6

Provenance & Evidence