Ethyl 1-methylpiperidine-4-carboxylate → 1-Methyl-4-piperidinemethanol

Participants

Reaction Steps

To an ice-cooled solution of 1-methyl-piperidine-4-carboxylic acid ethyl ester (0.855 g, 5 mmol) in THF (30 ml) was added dropwise a 1M solution of LiAlH4 in THF (20 ml, 20 mmol). The reaction mixture was then stirred for 18 h whilst warming to ambient temperature, and then quenched by careful addition of water (0.75 ml), 10% aqueous NaOH (0.75 ml) then water (3×0.75 ml) and stirred at ambient temperature for 2 h. The resultant mixture was reduced in vacuo, shaken with ethyl acetate and filtered to remove inorganic residues. The filtrate was reduced in vacuo to give (1-methyl-piperidin-4-yl)-methanol as a colourless oil (0.468 g, 73%). (LC/MS: Rt 0.33, [M+H]+ 130.20).

Provenance & Evidence