Hydrochloric Acid → N-Benzyl-N-[2-(5-ethynyl-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide

Participants

Reaction Conditions

Reaction Steps

To cyclohexene (0.12 mL, 1.14 mmol) in THF (0.3 mL) at 0° C. was added borane tetrahydrofuran complex (1M in THF; 0.53 mL, 0.53 mmol), and the reaction was stirred for 1.5 hours. N-Benzyl-N-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide (0.084 g, 0.15 mmol) in THF (2 mL) was added dropwise, and the reaction was stirred for 1 hour at room temperature. The mixture was cooled to 0° C., and MeOH (0.9 mL) was added, followed by 1N aqueous NaOH (0.53 mL, 0.53 mmol) and hydrogen peroxide (30%; 0.16 mL, 1.55 mmol), and the reaction was stirred for 1 hour at 0° C. and 1.5 hours at 40° C. The mixture was acidified with 1N aqueous HCl and extracted with EtOAc to give N-Benzyl-N-[2-(5-ethynyl-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide.

Provenance & Evidence