[NH:1]([C@@H:3]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][O:9][CH2:8]1)[CH2:4][OH:5])N>CO.[Ni]>[NH2:1][C@@H:3]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][O:9][CH2:8]1)[CH2:4][OH:5]To the solution of (2S)-2-hydrazinyl-3-(tetrahydro-2H-pyran-3-yl)propan-1-ol (5.79 g, 0.033 mol) in MeOH (100 mL) was added Raney Ni. The flask was degassed and equipped with a hydrogen inflated balloon. The flask was dipped into an ultrasound bath filled with water and sonicated for 4 hr at rt until the starting material was completely consumed. The mixture was then filtered through celite, and the filter cake was washed with MeOH (2×30 mL). Removal under reduced pressure gave (2S)-2-amino-3-(tetrahydro-2H-pyran-3-yl)propan-1-ol (5.4 g, 90%).
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