C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]1)C1C=CC=CC=1.[BrH:18].[H][H]>C(O)C.[Pd]>[BrH:18].[OH:17][CH2:16][CH2:15][O:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1A solution of (B) (12 g) in ethanol (200 ml) was neutralized with an ethanolic solution of hydrogen bromide and hydrogenated in the presence of 10% palladium on carbon (2.4 g). After 5 hours the uptake of hydrogen ceased and the catalyst was removed by filtration. The filtrate was taken to dryness in vacuo to give (C) as a semicrystalline solid.
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