Tetrahydrofuran → HCID 86641346, compound

Participants

Reaction Conditions

Reaction Steps

Lithium borohydride (67 mg) was added to a mixture composed of methyl {4-[bis(tert-butoxycarbonyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl}acetate of Example 111 (957 mg) and dehydrated tetrahydrofuran (18 ml) under ice-cooling. The mixture was stirred at 0° C. for two hours, and then returned to room temperature and stirred overnight. The mixture was ice-cooled again and lithium borohydride (33 mg) was added, followed by stirring at 0° C. for two hours. Methanol (6 ml) and a 1 N sodium hydroxide solution (6 ml) were added to the reaction mixture. Then, the mixture was returned to room temperature and stirred for four hours. The organic solvent in the reaction mixture was evaporated under reduced pressure. Then, a 0.2 N hydrochloric acid solution was added, followed by extraction with chloroform. The organic layer was washed with brine, and then dried over magnesium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (chloroform-methanol) to obtain the title compound (301 mg, 40%) as an oil.

Provenance & Evidence