Ethanol → HCID 20748464, compound

Participants

Reaction Steps

Ethanol (5 ml) and a saturated aqueous ammonium chloride solution (5 ml) were added to a tetrahydrofuran (5 ml) solution of (2S)-1-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-3,3-dimethyl-2-((2-nitrophenyl)amino)butan-1-one (395 mg, 0.92 mmol) obtained in Example 24, and the mixture was stirred at room temperature. Water was added to the reaction solution until the insoluble matter was dissolved, powdery iron (6 g) was added, and the mixture was refluxed with heating for 2 hours. The reaction solution was cooled to room temperature, and the excessive iron and tinorganic salt were filtered off using Celite. The filtrate was diluted with ethyl acetate (150 ml), washed with a 1 N aqueous sodium hydroxide solution (50 ml×2), dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography using ethyl acetate and hexane (1:1) and then chloroform and methanol (20:1) as eluents to obtain the captioned compound (321 mg, 87%) as a colorless foamy substance.

Provenance & Evidence