Methyl iodide → 1-tert-Butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of NaHMDS (2M in THF, 148 mmol, 74 mL, diluted to 100 mL) is cooled at −78° C. and a solution of piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (25.74 g, 100 mmol) in THF (50 mL of solution) is added slowly. The mixture is stirred for 2 h at −78° C. Methyliodide (7.5 mL, 120 mmol) is dissolved in THF (60 mL) and the cold solution of enolate is added. The mixture is stirred at r.t. for 1 h and quenched with HCl (1M, 75 mL) and ether (200 mL). the phases are separated and the organic phase washed with HCl (1M, 2×50 mL) and NaOH (1M, 2×50 mL). The organic phase is dried (Na2SO4), filtered and evaporated to provide the crude title compound.

Provenance & Evidence