Ethyl Acetate → HCID 9982364, compound

Participants

Reaction Steps

(2S,3S,4R)-6-nitro-4-[N-(4-chlorophenyl)-N-(2-methyl-2H-tetrazol-5-ylmethyl)amino]-3-hydroxy-2-methyl-2-dimethoxymethyl-3,4-dihydro-2H-1-benzopyran obtained in the example 1 (100 mg, 0.2 mmol) was dissolved in methanol (2 ml), thereto Cu(OAc)2 aqueous solution (0.38 ml, 0.4 M aqueous solution, 0.15 mmol) was added. Sodium borohydride (NaBH4) (113 mg, 3.0 mmol) was slowly added to the solution for 30 min at room temperature, the reaction mixture was stirred for 1 hours, thereafter ethyl acetate (5 ml) was added to the reaction mixture. The resulting mixture was filtered to remove precipitated black solid. Saturated NaHCO3 aqueous solution (5 ml) was added to the filtrate, and extracted with ethyl acetate (30 ml). The organic layer was washed with saturated brine solution, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (developing solvent-n-hexane:ethyl acetate=1:3), to give desired compound, the compound that R1 is substituted to amino group (62 mg, yield: 67%).

Provenance & Evidence