Sodium Azide → (S)-2-Azido-2-(6-(trifluoromethyl)pyridin-3-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (R)-5-(oxiran-2-yl)-2-(trifluoromethyl)pyridine (2.72 g, 14.4 mmol) in acetonitrile (200 mL) were added lithium perchlorate (20 g, 0.19 mol) and sodium azide (3.7 g, 57 mmol). The mixture was stirred at 60° C. overnight and TLC indicated completion of the reaction. After cooling, the mixture was filtered through Celite and the filtrate was concentrated. The residue was treated with water and extracted with EtOAc. The combined organic layers were dried, and concentrated. The residue was purified by silica gel column to afford the title compound.

Provenance & Evidence