2,2,6,6-Tetramethylpiperidine → HCID 13339631, compound

Participants

Reaction Conditions

Reaction Steps

To a dried tetrahydrofuran solution of 4.03 g of 2,2,6,6-tetramethylpiperidine under N2 was added 17.8 ml of 1.6M n-butyllithium in hexane. The solution was cooled to -75° C. and a concentrated solution of 4-(1-bromo-3,3,3-trichloro-1-methylpropyl)-2,6-dichloropyridine in tetrahydrofuran was added to maintain ≤-65° C. The mixture was stirred at -65° C. for two hours and quenched with 20 mls of water. The organics were extracted with ether, dried (MgSO4), and concentrated in vacuo. The crude product was purified via high pressure liquid chromatography, yielding 5 g (68%), m.p. 66°-67.5° C.

Provenance & Evidence