Methanol → HCID 23121838, compound

Participants

Reaction Steps

Bis(1,1-dimethylethyl)2-benzoyl-1,4-piperazinedicarboxylate (0.10 g, 0.26 mmol) was dissolved in methanol (2 mL), sodium borohydride (19 mg, 0.51 mmol) was added thereto, and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added ethyl acetate, and the resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (3 mL), 60% sodium hydride (12 mg, 0.30 mmol) was added thereto, and the mixture was stirred at room temperature for 1 hour. The resulting mixture was extracted with ethyl acetate, washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1) to obtain the title compound (47 mg, yield 57%) as a diastereomer mixture. Diastereomer ratio (α:β=1:5).

Provenance & Evidence