Acetic Acid → HCID 60026569, compound

Participants

Reaction Steps

To a solution of 3-[4,4,4-trifluoro-3-hydroxy-1,1-dimethyl-3-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)butyl]benzaldehyde (50 mg, 0.13 mmol), 3 mL of dichloroethane, and acetic acid (0.1 mL, 1.6 mmol) in an ice bath was added morpholine (0.28 mL, 3.20 mmol) in one batch. The solution was warmed to room temperature and stirred for 0.5 hours. Triacetoxy sodium borohyride (68 g, 0.32 mmol) was added in a single portion and the reaction stirred at room temperature for 3.0 hours. The solution was diluted with ethyl acetate and 3 mL of 3% ammonium hydroxide solution was added. The biphasic system was transferred to a separatory funnel and the aqueous layer was removed and back-extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and the solvent was evaporated in vacuo. The product was eluted from a flash chromatography column with dichloromethane-methanol, and evaporation of the solvent in vacuo yielded the title compound (27 mg, 45% yield).

Provenance & Evidence