Tetrahydrofuran → {5H,6H,7H,8H-imidazo[1,2-a]pyridin-6-yl}methanol

Temperature

0 °C

Suspend 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).

1. temperatureto warm to ambient temperature
2. waitAfter 15 minutes
3. temperaturecool the reaction mixture to 0° C.
4. filtrationAdd magnesium sulfate then filter the reaction mixture
5. washrinsing the filter cake with 200 mL dichloromethane
6. concentrationConcentrate the filtrate

ORD record

ord-0506e87b3ef04de5b8f0977525d5b63c

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394317B2