[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@@H:8]([N:11]=[N+]=[N-])[C@H:7]([OH:14])[CH2:6]1)=[O:4]>CO.C(O)(=O)C.[Pd]>[C:3]([OH:4])(=[O:2])[CH3:5].[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@@H:8]([NH2:11])[C@H:7]([OH:14])[CH2:6]1)=[O:4]A solution of azide (b) (18.4 g, 92 mmol) in methanol/acetic acid (360 ml/40 ml) was hydrogenated over 10% palladium on charcoal paste (50% w/w with water, 15 g) for 18 hours. The mixture was filtered through keiselguhr, evaporated, and then triturated with ether to afford a white solid that was isolated by filtration and dried in vacuo (15.6 g, 72%).
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