Methyl iodide → Tert-butyl 4-methyl-3-oxopiperazine-1-carboxylate

Participants

Reaction Steps

To a solution of 3-oxopiperazine-1-carboxylic acid tert-butyl ester (500 mg, 2.50 mmol) in DMF (20 mL) cooled on an ice-bath was added sodium hydride (120 mg, 3.00 mmol, 60% dispersion in mineral oil) and the resulting mixture stirred for 10 min. Methyl iodide (233 μL, 532 mg, 3.75 mmol) was added and the resulting mixture stirred at room temperature for 18 h. The reaction mixture was quenched with H2O and extracted with EtOAc. The combined organics were dried (Na2SO4) and concentrated in vacuo affording 4-Methyl-3-oxopiperazine-1-carboxylic acid tert-butyl ester as a yellow oil (300 mg, 56%). 1H NMR (CDCl3, 300 MHz): δ 4.08 (s, 2 H); 3.65 (t, J=5.4 Hz, 2 H); 3.35 (t, J=5.4 Hz, 2 H); 3.00 (s, 3 H); 1.47 (s, 9 H).

Provenance & Evidence