3-(benzhydrylamino)-3-methylbutan-2-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 3-(benzhydrylamino)-3-methylbutan-2-one (6.5 g) in acetic acid (20 mL), HCl gas was blown up to saturation, and bromine (1.25 mL) was added dropwise thereto, followed by stirring for 3 hours. 20% Aqueous sodium hydroxide was added to the reaction mixture, and thereby pH of the mixture was adjusted at 14 or higher, followed by partitioning by use of carbon tetrachloride. The organic layer was washed with water. The solvent was evaporated under reduced pressure, and to the residue, N,N-dimethylformamide (30 mL) and saturated aqueous sodium hydrogencarbonate (7 mL) were added, followed by stirring for 3 minutes. The reaction mixture was partitioned between water and carbon tetrachloride. The organic layer was washed twice with saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and the residue was purified through silica gel column chromatography, to thereby give 1-benzhydryl-2,2-dimethylazetidin-3-one as a solid (754 mg, 12%). was added dropwise by partitioning by use of carbon tetrachloride The organic layer was washed with water The solvent was evaporated under reduced pressure to the residue, N,N-dimethylformamide (30 mL) and saturated aqueous sodium hydrogencarbonate (7 mL) were added by stirring for 3 minutes The reaction mixture was partitioned between water and carbon tetrachloride The organic layer was washed twice with saturated brine dried over magnesium sulfate anhydrate followed by filtration The solvent was evaporated under reduced pressure the residue was purified through silica gel column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the above-obtained 3-bromo-3-methylbutan-2-one (5.88 g) in methanol (30 mL), benzhydrylamine (5.0 mL) and triethylamine (7.5 mL) were added. The resultant mixture was stirred at 70° C. for 24 hours, and then cooled in air. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was sequentially washed with saturated aqueous sodium hydrogencarbonate and saturated brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, and to the solid, diethyl ether was added, and then insoluble matter was removed by filtration. The mother liquid was brought to the dryness under reduced pressure. The residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give 3-(benzhydrylamino)-3-methylbutan-2-one as an oily product (3.3 g, 34%). cooled in air The reaction mixture was partitioned between water and ethyl acetate The organic layer was sequentially washed with saturated aqueous sodium hydrogencarbonate and saturated brine dried over magnesium sulfate anhydrate followed by filtration The solvent was evaporated under reduced pressure to the solid, diethyl ether was added insoluble matter was removed by filtration The residue was purified through silica gel column chromatography (hexane-ethyl acetate)