1-propan-2-ylpyrrolidin-2-one

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4N sodium hydroxide (36 ml) was added to 1-isopropyl-2-pyrrolidone (9.2 g), and the mixture was stirred for 3.5 hours. After cooled to 0° C., the mixture was neutralized with concentrated hydrochloric acid. After sodium carbonate (15.3 g) was added thereto, a solution of 5-bromo-2-fluorobenzaldehyde (7.3 g) in dimethyl sulfoxide (96 ml) was added thereto, and the mixture was heated to reflux for 5 hours. After cooled to room temperature, pH was adjusted to approximate 4 with 6N hydrochloric acid, and the mixture was extracted with ethyl acetate/THF. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1→3/2) to give 4-(4-bromo-2-formylisopropylanilino)butyric acid (0.92 g). the mixture was heated to reflux for 5 hours After cooled to room temperature the mixture was extracted with ethyl acetate/THF The extract was washed with saturated brine dried with magnesium sulfate The solvent was removed under reduced pressure the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1→3/2)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4N sodium hydroxide (36 ml) was added to 1-isopropyl-2-pyrrolidone (9.2 g), and the mixture was stirred for 3.5 hours. After cooled to 0° C., the mixture was neutralized with concentrated hydrochloric acid. After sodium carbonate (15.3 g) was added thereto, a solution of 5-bromo-2-fluorobenzaldehyde (7.3 g) in dimethyl sulfoxide (96 ml) was added thereto, and the mixture was heated to reflux for 5 hours. After cooled to room temperature, pH was adjusted to approximate 4 with 6N hydrochloric acid, and the mixture was extracted with ethyl acetate/THF. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1→3/2) to give 4-(4-bromo-2-formylisopropylanilino)butyric acid (0.92 g). the mixture was heated to reflux for 5 hours After cooled to room temperature the mixture was extracted with ethyl acetate/THF The extract was washed with saturated brine dried with magnesium sulfate The solvent was removed under reduced pressure the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1→3/2)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4N sodium hydroxide (36 ml) was added to 1-isopropyl-2-pyrrolidone (9.2 g), and the mixture was stirred for 3.5 hours. After cooled to 0° C., the mixture was neutralized with concentrated hydrochloric acid. After sodium carbonate (15.3 g) was added thereto, a solution of 5-bromo-2-fluorobenzaldehyde (7.3 g) in dimethyl sulfoxide (96 ml) was added thereto, and the mixture was heated to reflux for 5 hours. After cooled to room temperature, pH was adjusted to approximate 4 with 6N hydrochloric acid, and the mixture was extracted with ethyl acetate/THF. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1→3/2) to give 4-(4-bromo-2-formylisopropylanilino)butyric acid (0.92 g). the mixture was heated to reflux for 5 hours After cooled to room temperature the mixture was extracted with ethyl acetate/THF The extract was washed with saturated brine dried with magnesium sulfate The solvent was removed under reduced pressure the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1→3/2)