HCID 7586306, compound → HCID 68565785, compound

Participants

Reaction Steps

Diisobutylaluminum hydride (1M, 2.53 mL, 2.53 mmol) was added to a solution of methyl N-{[(1-benzylpiperidin-4-yl)amino]carbonyl}phenylalaninate (800 mg, 2.02 mmol) in toluene (7.5 mL) and dichloromethane (7.5 μL) at −78° C. and stirred for 30 min and then warmed to ambient temperature. After 5 min at room temperature, the reaction was quenched with saturated potassium sodium tartrate solution (20% solution), extracted with dichloromethane and treated with a 4 N HCl solution (50 mL). After 30 min. the mixture was extracted with water, basified to pH=7, and extracted with dichloromethane (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica gel, 0 to 8% {1% ammonium hydroxide/methanol} in methylene chloride gradient elution), gave the title compound (250 mg). MS 348.3 (M+1)

Provenance & Evidence