[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:20](OCC)=[O:21])([CH3:19])[CH3:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[Na]>CCOCC.O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]([CH3:19])([CH3:18])[CH2:20][OH:21])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1A solution of 4-(1-ethoxycarbonyl-1-methyl-ethyl)-piperazine-1-carboxylic acid benzyl ester (3.5 g, 10.5 mmol) in 10 mL of dry ether was slowly added to a suspension of lithium aluminium hydride (0.3 g, 105 mmol) in tetrahydrofuran at −15° C. under nitrogen and the resulting mixture was stirred at 0° C. for 3 hours. On cooling, the mixture was treated dropwise with water (0.3 mL), aqueous sodium hydroxyde (0.3 mL, 4N), and water (0.9 mL) and filtered. The filtrate was concentrated under reduced pressure to yield 4-(2-hydroxy-1,1-dimethyl ethyl)piperazine-1-carboxylic acid benzyl ester as a white solid (1.2 g, 41%).
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