C([O:8][C@H:9]1[C@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[CH2:12][N:11]([CH2:31][CH2:32][CH2:33][Cl:34])[C@@H:10]1[CH2:35][O:36]CC1C=CC=CC=1)C1C=CC=CC=1.Cl>C(O)C.[Pd]>[Cl:34][CH2:33][CH2:32][CH2:31][N:11]1[CH2:12][C@H:13]([OH:23])[C@@H:14]([OH:15])[C@H:9]([OH:8])[C@H:10]1[CH2:35][OH:36]To a stirred solution of (2R,3R,4R,5S)-3,4,5-tris(benzyloxy)-2-[(benzyloxy)methyl]-1-(3-chloropropyl)piperidine 4 (30 g, 49.98 mmol) in a mixture of ethanol (1.2 lit) and aqueous solution of HCl (1M, 100 mL) was added 10% Pd/C (3 g) and the mixture was degassed for 20 min using nitrogen. The reaction mixture was then stirred under 50 psi hydrogen pressure for 32 h. The reaction mixture was filtrate through celite, washed with ethanol (3×100 mL) and the filtrate was concentrated under reduced pressure to get crude hydrochloride salt of (2R,3R,4R,5S)-1-(3-chloropropyl)-2-(hydroxymethyl)piperidine-3,4,5-triol 5 (10 g, 83%) as black oil.
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