[CH:1]1([S:4][C:5]2[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=O)=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH:1]1([S:4][C:5]2[CH:13]=[CH:12][C:8]([CH2:9][NH2:11])=[CH:7][CH:6]=2)[CH2:2][CH2:3]1A solution of 4-cyclopropylsulfanyl-benzamide (preparation 31a, 137 mg, 0.71 mmol) in dry tetrahydrofuran (1.0 mL) is added at 0° C. to a solution of lithium aluminium hydride in tetrahydrofuran (1 M, 2.1 mL, 2.1 mmol). The mixture is stirred at 0° C. for 1 h and heated at reflux for 1 h. The mixture is cooled at room temperature and stirred for 1.5 h. Water is added, and the mixture is extracted twice with dichloromethane. The combined organic layers are dried over Na2SO4 and concentrated under reduced pressure. Yield: 75 mg (60% of theory); ESI mass spectrum: [M+H]+=180; Retention time HPLC: 0.51 min (X011_S03).
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