Chlorotrimethylsilane → 2-(2-Cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethanamine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of lithium borohydride (232 μL, 0.465 mmol) in THF was added chlorotrimethylsilane (118 μL, 0.930 mmol) dropwise. After stirring for 15 minutes, argon was bubbled through the reaction mixture for 2 minutes to eliminate any trimethylsilane in the reaction mixture. (E)-2-cyclopropyl-3-(2-nitrovinyl)-6-(trifluoromethyl)pyridine (30 mg, 0.116 mmol) was added (in 1 mL of THF). The reaction was heated to reflux for 2 hours, cooled to 0° C. and carefully quenched with methanol (1 mL). The reaction mixture was concentrated, diluted with dichloromethane and 20% aqueous KOH. The layers were separated and the organic layer was dried over sodium sulfate, filtered and concentrated to yield 2-(2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)ethanamine (26 mg, 0.113 mmol, 97.2% yield).

Provenance & Evidence