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

Participants

Reaction Conditions

Reaction Steps

Piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (1.00 g, 4.11 mmol) is dissolved in THF (10 mL) and cooled to −78° C. 2.0 M Lithium diisopropyl amide in THF is added dropwise, then stirred for 1 hour. Iodomethane (0.563 mL, 9.04 mmol) is added and the mixture is stirred for 1 hour. The cold bath is removed and the reaction stirred for an additional 0.5 hour. The reaction mixture is quenched with saturated ammonium chloride (3 mL), concentrated, taken up in dichloromethane, and chromatographed on silica gel, eluting with EtOAc in dichloromethane 0-5%, to give the title compound as a slightly yellow oil. (680 mg, 64% yield).

Provenance & Evidence