Br.[OH:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[NH:10][C:11]1[S:12][CH:13]=[C:14]([C:16](OCC)=[O:17])[N:15]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[NH:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][OH:17])[N:15]=10.02 mole of the product obtained in Example 2 is added in small portions at room temperature to a suspension of 0.05 mole of lithium aluminium hydride in 100 ml of anhydrous THF. Stirring is maintained for 1 hour at room temperature, the mixture is cooled and the excess hydride destroyed by adding water, the solid is allowed to drain and the filtrate is evaporated under vacuum on a water bath. The oily residue is then crystallized in ether and recrystallized in a methanol/ether mixture. (M.p. 188°-90° C.). Yield: 30%.
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