Tributylstannane → Tert-butyl 1-(6-(tributylstannyl)pyrazin-2-yl)piperidin-3-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tri-n-butyltin hydride (1.686 mL, 6.39 mmol) in THF (10 mL) at 0° C. was added LDA (1.8 M solution in heptane/THF/ethylbenzene, 3.55 mL, 6.39 mmol) dropwise. The reaction mixture was stirred at 0° C. for 15 min and tert-butyl 1-(6-chloropyrazin-2-yl)piperidin-3-ylcarbamate (1.00 g, 3.20 mmol) was added. The reaction mixture was kept at 0° C. for 2 h, then quenched with 10% KF solution. The mixture was extracted with DCM and the combined organic layers were dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 10-25% EtOAc in Hexanes) to give tert-butyl 1-(6-(tributylstannyl)pyrazin-2-yl)piperidin-3-ylcarbamate (400 mg, 22.1% yield). MS (ESI, pos. ion) m/z: 569 (M+1).

Provenance & Evidence