[OH:1][CH2:2][C@@H:3]([N:11](C([O-])=O)[NH:12]C([O-])=O)[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][O:7][CH2:6]1>CO.[OH-].[OH-].[Pd+2]>[NH:11]([C@@H:3]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][O:7][CH2:6]1)[CH2:2][OH:1])[NH2:12]To the solution of 1-((2S)-1-hydroxy-3-(tetrahydro-2H-pyran-3-yl)propan-2-yl)hydrazine-1,2-dicarboxylate (14.68 g, 0.0332 mol) in methanol (250 mL) was added Pd(OH)2/C (1.47 g). The reaction flask was degassed and filled into H2. Stirring was continued until the starting material disappeared. When the reaction was over, the mixture was filtered through celite, and the filter cake was washed with MeOH (2×20 mL). The combined organic solvent was dried over Na2SO4, and concentrated in vacuo to give (2S)-2-hydrazinyl-3-(tetrahydro-2H-pyran-3-yl)propan-1-ol (5.79 g, 94%), which was used for the next step without purification.
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