Piperidin-4-ol → HCID 121249534, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-2-(4-methoxybenzyloxy)pyridine (7.25 g, 24.65 mmol), 4-hydroxypiperidine (3.74 g, 36.97 mmol), tris(dibenzylideneacetone)dipalladium (451 mg, 0.493 mmol), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (614 mg, 0.986 mmol), and sodium-t-butoxide (3.32 g, 34.51 mmol) in anhydrous toluene (90 ml) was heated at 85° C. under nitrogen for 22 hours. The reaction mixture was diluted with ethyl acetate, washed with sat'd NaCl(aq.), dried (MgSO4), filtered, and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 1:1 hexanes: EtOAc to 3:7 hexanes: EtOAc) gave the title compound as a brown, viscous oil (4.45 g, 57%).

Provenance & Evidence