[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 with H2. 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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