Cl.[N:2]1[CH:3]=[CH:4][N:5]2[CH2:10][CH:9]([C:11](OCC)=[O:12])[CH2:8][CH2:7][C:6]=12.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>ClCCl.O>[N:2]1[CH:3]=[CH:4][N:5]2[CH2:10][CH:9]([CH2:11][OH:12])[CH2:8][CH2:7][C:6]=12Suspend ethyl 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6-carboxylate hydrochloride (5.74 g; 1.0 equiv; 24.88 mmoles) in dichloromethane (100 mL), and tetrahydrofuran (40 mL) and cool to 0° C. Add lithium aluminum hydride (1.77 g; 1.8 equiv; 44.79 mmoles) portionwise over 10 minutes. After an additional 5 minutes, allow the reaction mixture to warm to ambient temperature. After 15 minutes, cool the reaction mixture to 0° C. and slowly add water (1.77 mL), 15% sodium hydroxide solution (1.77 mL), and water (5.31 mL) sequentially with vigorous stirring. Continue to stir at ambient temperature for 15 minutes. Add magnesium sulfate then filter the reaction mixture, rinsing the filter cake with 200 mL dichloromethane. Concentrate the filtrate to give 5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ylmethanol (2.63 g; 69%). MS (m/z): 153(M+1).
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