CCOCC.[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]([CH2:26][N+:27]([O-])=O)[CH2:21][C:22](OC)=[O:23])[CH:16]=[CH:17][C:18]=1[Cl:19]>O1CCCC1>[NH2:27][CH2:26][CH:20]([C:15]1[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([Cl:12])[CH:14]=1)[CH2:21][CH2:22][OH:23]To a 1M Et2O solution of LiAlH4 (200 mL, 200 mmol) at 0° C., slowly add the product of Step 2 (14.35 g, 49.1 mmol) dissolved in tetrahydrofuran (THF) (100 mL). Allow the reaction mixture to warm to room temperature and stir for 45 min. After recooling to 0° C., quench the excess LiAlH4 by the careful addition of aqueous saturated Na2SO4 (20 mL). Dry the solution with Na2SO4 and filter. Wash the lithium salts with Et2O (3×300 mL). Concentrate the combined filtrates to give 8.65 g of 4-amino-3-(3,4-dichlorophenyl)-butanol as a white solid (36.9 mmol, 75%).
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