[BH4-].[Na+].B(F)(F)F.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=O)[C:16]1[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:19]([OH:26])=[C:18]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:17]=1.Cl>O1CCCC1>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH2:15][C:16]1[CH:17]=[C:18]([C:27]([CH3:28])([CH3:29])[CH3:30])[C:19]([OH:26])=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1To a suspension of sodium borohydride (2.72 g) in tetrahydrofuran (80 ml) was added dropwise under ice-cooling BF3, Et20 (8.86 ml) and the mixture was stirred for 30 minutes. To this mixture was added by portions N-(2-aminophenyl )-3,5-di-t-butyl-4-hydroxybenzamide (3.06 g ) and the mixture was stirred overnight while returning slowly to room temperature. 6N hydrochloric acid war added and the mixture was heated under reflux for 30 minutes, the solvent was distilled off and the residue was placed into water, neutralized with sodium hydrogen carbonate, extracted with ethyl acetate, washed with water and saturated saline and dried over anhydrous MgSO4. The solvent was distilled off and the residue was purified by a silica gel column chromatography (hexane:ethyl acetate=4:1) to give (2-aminophenyl)-3,5-di-t-butyl-4-hydroxybenzylamine (2.00 g, 68%) as crystals.
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