[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([C:23](OCC)=[O:24])([CH3:22])[CH3:21])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>O1CCCC1>[C:7]([O:11][C:12]([N:14]1[CH2:15][CH2:16][N:17]([C:20]([CH3:22])([CH3:21])[CH2:23][OH:24])[CH2:18][CH2:19]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]To a suspension of lithium aluminium hydride powder (0.324 g) in anhydrous tetrahydrofuran (30 mL) at 0° C. under argon was added 4-(1-ethoxycarbonyl-1-methyl-ethyl)-piperazin-1-carboxylic acid tert-butyl ester (1.28 g). The reaction mixture was allowed to warm to room temperature and stirred for 2 hours, then quenched with saturated aqueous ammonium chloride (10 mL). The reaction mixture was partitioned between water and dichloromethane and the combined organic layers washed with brine and dried (MgSO4). The solution was evaporated to give 4-(2-hydroxy-1,1-dimethyl-ethyl)-piperazin-1-carboxylic acid tert-butyl ester (0.43 g).
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