Ethyl Acetate → HCID 69216674, compound

Participants

Reaction Steps

(2R,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 (100 mg, 0.2 mmol) prepared in example 109 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. To the solution sodium borohydride (NaBH4, 113 mg, 3.0 mmol) was slowly added at the room temperature for 30 min. The reaction mixture was stirred for 1 hour, thereto ethyl acetate (5 ml) was added. The reaction mixture was filtered to remove the black precipitation. NaHCO3 aqueous solution (5 ml) was added to the resulting filtrate. The filtrate was extracted with ethyl acetate (30 ml). The organic layer was washed with saturated brine solution, dried over magnesium sulfate and concentrated. The crude product was purified by silica gel column chromatography (developing solvent-n-hexane:ethyl acetate=1:3), to give desired compound (58 mg, yield: 62%).

Provenance & Evidence