2-Methylpyrrolidine → HCID 11748944, compound

Participants

Reaction Steps

2.2 g (6.85 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, 2.41 ml (13.9 mmol) of N,N-diisopropylethylamine and 0.27 g (2.0 mmol) of 1-hydroxy-1H-benzotriazole are added successively to a solution of 1.9 g (6.31 mmol) of 4-bromo-2-ethoxycarbonylmethyl-5-methyl-benzoic acid in 660 ml of tetrahydrofuran/H2O (9:1). After 10 minutes' stirring, 0.59 g (6.94 mmol) of rac-2-methyl-pyrrolidine is added, the mixture is stirred for another 19 hours and then diluted with 200 ml of ethyl acetate. The solution obtained is washed with 14% NaCl solution and extracted 2× with ethyl acetate. The combined organic phases are washed with 14% NaCl solution and dried with Na2SO4. After removal of the solvent, by distillation, and flash chromatography (silica gel; methylene chloride/ethanol=98:2) the desired compound is obtained.

Provenance & Evidence