o-Toluenesulfonyl chloride → (S)-4-(1-azido-ethyl)-pyridine

Participants

Reaction Conditions

Reaction Steps

(R)-1-Pyridin-4-yl-ethanol (0.160 g) was dissolved in THF (10 mL) and cooled to 0° C. nBuLi (2.5 M in hexanes, 0.52 mL) was added slowly and the reaction was stirred at 0° C. for 5 min. Toluenesulfonyl chloride (0.250 g) was added and the stirring was continued for 30 min. NaN3 (0.30 g) was added, the reaction was warmed to RT and stirred overnight. The mixture was added to H2O and the layers were separated. The aqueous layer was extracted with Et2O and the combined organic phases were dried over Na2SO4, filtered and evaporated in vacuo to yield a yellow oil. This crude material was purified by silica gel chromatography (30 g, 33 to 75% Et2O/hexanes w/1% Et3N) to afford (S)-4-(1-azido-ethyl)-pyridine as a clear oil.

Provenance & Evidence