Methyl iodide → 1-[(Tert-butoxy)carbonyl]-4-methoxypiperidine-4-carboxylic acid

Participants

Reaction Steps

A mixture of 0.415 g (1.52 mmol) 4-Hydroxy-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester, 68 mg (1.97 mmol) NaH (55% in oil) and 0.3 g (2.12 mmol) iodomethane in 10 mL DMF was stirred for 2 h at room temperature. Water was added and the mixture was concentrated to dryness. The residue was dissolved in THF and water and 0.254 g (6 mmol) LiOH.H2O wad added and the mixture was stirred for 16 h at room temperature. After evaporation the residue was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid to yield after evaporation of the product containing fractions 49.7 mg (13%) of the title compound as white solid. MS (m/e): 258.1 [(M−H)].

Provenance & Evidence