Acetic Acid → tert-butyl 4-(4-((S)-1-(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-ylamino)ethyl)benzyl)-2,2-dimethylpiperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 4-((S)-1-(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-ylamino)ethyl)benzaldehyde (71 mg, 0.2 mmol) and tert-butyl 2,2-dimethylpiperazine-1-carboxylate (47.1 mg, 0.22 mmol) in MeOH (4 mL) was added acetic acid (14.4 mg, 0.24 mmol) and 5-Ethyl-2-methylpyridine borane complex (27 mg, 0.2 mmol, sigma aldrich). The solution was stirred at 50° C. for 4 h then 5 drops of water was added. The solution was stirred at room temperature for another 2 h then diluted with EtOAc (10 mL) and washed with water (10 mL). After separation, the aqueous phase was extracted with EtOAc (3×10 mL). Combined organics were dried over Na2SO4, filtered and concentrated. The crude material was purified through Silica gel column chromatography (MeOH/EtOAc 0 to 10%) to give tert-butyl 4-(4-((S)-1-(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-ylamino)ethyl)benzyl)-2,2-dimethylpiperazine-1-carboxylate as a white solid (80 mg, 72.4% yield).

Provenance & Evidence