[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:14][C:13]([CH2:15][C:16]#[N:17])=[C:12]([CH2:18][Br:19])[CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[C:1]1([CH3:20])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH2:11][C:12]([CH2:18][Br:19])=[C:13]([CH2:15][CH2:16][NH2:17])[CH2:14]2)(=[O:9])=[O:8])=[CH:5][CH:6]=14 g of N-(p-toluenesulfonyl)-3-(bromomethyl)-4-(cyanomethyl)-3-pyrroline, prepared in Preparation 6, was dissolved in 100 ml of ethyl ether. The solution was slowly added to the suspension of 1 g of lithium aluminum hydride (LAH) in 20 ml of ethyl ether, and heated with refluxing for 3 hours. The reaction mixture was cooled by ice water. After adding 3 ml of water, it was stirred for 30 minutes and filtered off. The filtrate was concentrated. 2 g of the title compound was obtained (yield 49%).
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