Chlorotrimethylsilane → HCID 67287340, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of lithium borohydride (1226 μL, 2.45 mmol) in THF was added chlorotrimethylsilane (622 μl, 4.90 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)-6-cyclopropyl-2-methoxy-3-(2-nitrovinyl)pyridine (135 mg, 0.613 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-(6-cyclopropyl-2-methoxypyridin-3-yl)ethanamine (118 mg, 0.614 mmol, 100% yield).

Provenance & Evidence