[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:7]=1[C:8](OC)=[O:9].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC.[F-].[Na+].O>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:7]=1[CH2:8][OH:9]A solution of methyl 2-(2-(dimethylamino)ethylamino)-3-fluorobenzoate (749 mg, 3.117 mmol) in Et2O (30 mL) at −20° C. was treated with LAH (166 mg, 4.374 mmol). After 1.5 hours, additional LAH (15 mg, 0.3952 mmol) was added and the reaction was warmed to 0° C. After 1 hour at 0° C., the reaction was diluted with Et2O (70 mL) and NaF and water were added with vigorous stirring until the reaction was quenched and a white ppt formed. The clear solution was decanted and evaporated under vacuum. The crude material was purified on a 12 g ISCO redisep column (0-10% MeOH in CH2Cl2 as eluent) to yield 543 mg (82%) of (2-(2-(dimethylamino)ethylamino)-3-fluorophenyl)methanol as a clear oil. FIA: 213.08 (M+1).
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