3-Benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidin-2-one → (+)-3-Benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidine

Participants

Reaction Steps

To a solution of (−)-3-benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidin-2-one (1.73 g, 5.3 mmol) in THF (21 ml), LiAlH4 (6.5 ml of a 1 M solution in THF, 6.5 mmol) is added dropwise at rt. The mixture is refluxed for 2.5 h, cooled to rt, quenched with water and filtered over Celite®. The filtrate is evaporated, the residue dissolved in AcOEt, washed with water and brine, and the aq. layers are reextracted with AcOEt, the combined organic layers are dried over Na2SO4 and evaporated to give (+)-3-benzo[1,3]dioxol-5-ylmethyl-1-benzyl-piperidine ([α]Drt=28.2° (c=0.5, EtOH)).

Provenance & Evidence