C([N:8](CC1C=CC=CC=1)[C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH:16]2OCC[O:17]2)=[CH:11][C:10]=1[CH3:21])C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CCO.CCOC(C)=O.[Pd]>[NH2:8][C:9]1[C:10]([CH3:21])=[CH:11][C:12]([CH2:16][OH:17])=[C:13]([CH3:15])[CH:14]=1A stirred solution of dibenzyl-[4-(1,3-dioxolan-2-yl)-2,5-dimethylphenyl)amine (2.00 g, 5.35 mmol) in EtOH (14.0 mL) and EtOAc (7.00 mL) was flushed with nitrogen for 3 min and then sodium bicarbonate (0.200 g, 2.38 mmol) and palladium on activated carbon (10 wt. %, ˜50% water; 0.800 g, 0.360 mmol) were added. The reaction mixture was flushed with hydrogen gas for 3 min and then stirred under a hydrogen atmosphere (balloon) for 3 h. The mixture was then filtered through a pad of Celite and the pad washed with MeOH (10 mL). The filtrate was concentrated under reduced pressure to give the title compound, which was used without any further purification.
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