Sodium hydride → [(2R)-4-methylmorpholin-2-yl]methyl 4-phenylpiperazine-1-carboxylate

Participants

Reaction Steps

(R)-(4-Methyl-morpholin-2-yl)-methanol (Intermediate 11; 100 mg, 0.76 mmol) was added to a suspension of NaH (60% dispersion in oil; 90.0 mg, 2.28 mmol) in anhydrous THF (7 mL) and stirred under nitrogen for 30 min. 4-Nitrophenyl 4-phenylpiperazine-1-carboxylate (Intermediate 2; 300 mg, 0.92 mmol) was added and the reaction mixture was stirred at room temperature for 48 h. The reaction mixture was filtered through celite and the solid washed with THF (10 mL). The filtrates were combined and the solvent removed in vacuo. The residue was purified by column chromatography (normal phase silica, 5 g Isolute-Si column, gradient 1-5% MeOH in DCM). The solvents were removed in vacuo to give [(2R)-4-methylmorpholin-2-yl]methyl 4-phenylpiperazine-1-carboxylate (175 mg, 72%) as a light yellow gum

Provenance & Evidence