3,3-Dimethylbutanoyl chloride → 1-(3,3-Dimethyl-butyryl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Participants

Reaction Steps

To a solution of 4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.646 g) under an argon atmosphere were added triethylamine (0.668 g, 0.92 ml) and tert-butyl acetyl chloride (0.44 g, 0.45 ml) under ice cooling. The reaction mixture was stirred at RT for 3 h. It was then partitioned between methylene chloride and aqueous 1M HCl, the layers were separated and the aqueous layer washed with 2M aqueous KHCO3 and dried over Na2SO4. The solvent was evaporated off, the residue purified by flash chromatography (AcOEt/heptane, gradient from 0 to 50%) to give 1-(3,3-Dimethyl-butyryl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester, (0.46 g) as a light yellow solid. MS (ESI): 314 (MH+).

Provenance & Evidence