Sodium Bicarbonate → Tert-Butyl(2S)-4-(1-((benzyloxy)carbonyl)azetidin-3-yl)-2-methylpiperazine-1-carboxylate

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Reaction Steps

To a mixed solution of benzyl 3-oxoazetidine-1-carboxylate (30.0 g, 146 mmol), which is a known and commercially available product, THF (100 mL) and acetic acid (60 mL) was added a commercially available product of tert-butyl(2S)-2-methylpiperazine-1-carboxylate (32.2 g, 161 mmol) at room temperature. The resultant mixture was stirred at room temperature for 1 hour. To the reaction mixture was added sodium triacetoxyborohydride (46.5 g, 219 mmol) at 0° C. The resultant mixture was stirred at room temperature for 1 hour and 30 minutes. To the reaction mixture were added sodium hydrogen carbonate and water at 0° C. The resultant solution was extracted with ethyl acetate. An organic layer was dried over anhydrous magnesium sulfate and then filtrated. The solvent was evaporated under a reduced pressure, and the resultant residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=5:1) to give the title compound (36.7 g, yield: 64%).

Provenance & Evidence