Hydrochloric Acid → 4-Ethyl-3-(3-chlorophenyl)-1-(3-isopropylphenyl)pyrrolidine-2-one

반응식

[CH2:1]([C:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=2)[C:5](=[O:17])[C:4]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[CH3:2].B.[Na].Cl>C(O)C>[CH2:1]([CH:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=2)[C:5](=[O:17])[CH:4]1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[CH3:2]

참가 물질

실험 절차

5.0 g (14.7 mmol) of 4-ethyl-3-(3-chlorophenyl)-1-(3-isopropylphenyl)-3-pyrroline-2-one synthesized in Example 4 were dissolved in 50 ml of ethanol, and 0.56 g (14.7 mmol) of sodium boron hydride were added thereto little by little at room temperature under stirring. Reaction was further allowed to proceed at the same temperature for 1 hour, and the reaction mixture was then poured into 1 N hydrochloric acid, followed by extraction with ethyl acetate. The resultant organic layer was washed with water, an aqueous saturated sodium bicarbonate solution and water in this order, and then dried over magnesium sulfate. Next, the solvent was distilled off under reduced pressure. The resultant residue was analyzed by high-speed liquid chromatography (column: YMC-A302 (ODS), mobile phase: MeCN/H2O=9/1 (v/v), UV: 254 nm), and as a result, it was apparent that the residue was a mixture of the starting material/the end product=3/1 and a large amount of the raw material remained.