Water → N-Benzyl-3-(2-hydroxyethyl)pyridine-4-carboxamide

Participants

Reaction Steps

Butyl lithium (61.5 mL of a 1.6 M solution in hexane, 98.5 mmol) was added dropwise over 10 min to a stirred solution of N-benzyl-4-pyridinecarboxamide (9.94 g, 46.9 mmol) in THF (200 mL) at −78° C. under N2. The reaction mixture immediately turned dark blue, and was stirred for 1 h. A solution of ethylene oxide (2.27 g, 51.6 mmol) in dioxane (10 mL) was then added and the resulting mixture stirred at −78° C. for 3 h, after which time it was warmed to room temperature and quenched with MeOH (40 mL). The quenched reaction mixture was poured into H2O (200 mL) and extracted with EtOAc (3×150 mL). The combined organic extracts were washed with brine (150 mL), dried (MgSO4) and concentrated under reduced pressure. The crude material was purified by column chromatography on silica using 5–10% MeOH in DCM as the eluent to yield the desired alcohol (2.9 g, 24%). MS (ES+) 257 (M+1).

Provenance & Evidence