3-bromo-1-cyclohexylpyrrolidin-2-one

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Place 2,4-dichloro-benzenethiol (728 mg, 4.1 mmol) in tetrahydrofuran (10 mL) and cool to 0° C. Slowly add sodium hydride (98 mg, 4.1 mmol) and stir for 30 minutes. To this solution, add a solution of 3-bromo-1-cyclohexyl-pyrrolidin-2-one (Preparation 1) in tetrahydrofuran (2 mL) and stir at room temperature for 30 minutes. Pour reaction mixture onto ice and extract with methylene chloride. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (20-30% ethyl acetate in hexane) to yield 641 mg (92%) of the title compound: Mass spectrum (apci) m/z=344.1 (M+H). Pour reaction mixture onto ice extract with methylene chloride Dry over sodium sulfate filter concentrate Purify by silica gel (20-30% ethyl acetate in hexane)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolve 2,4-dibromo-butyryl chloride (17.0 g, 64.3 mmol) in chloroform (3 ml) and add to a mixture of cyclohexylamine (7.65 g, 77.2 mmol) in chloroform (20 mL) and H2O (3 mL) at 0° C. Add sodium hydroxide (5.92 g, 147.9 mmol) slowly while keeping the reaction temperature below 10° C. Stir for 1 hour. Wash the organic layer with 0.5M hydrochloride and brine. Dry over sodium sulfate, filter, and concentrate. Place the residue in THF (200 mL) and cool to 0° C. Add sodium hydride (1.02 g, 42.6 mmol) and stir for two days. Add additional sodium hydride (1.02 g, 42.6 mmol) and stir for 3 days. Pour onto water and ice and extract with methylene chloride. Dry over sodium sulfate, filter, and concentrate to yield 6.36 g (34%) of the title compound: NMR (CDCl3) δ 4.41 (dd, 1H), 3.94 (m, 1H), 3.48 (m, 1H), 3.33 (m, 1H), 2.51 (m, 1H), 2.30 (m, 1H), 1.82 (m, 3H), 1.70 (m, 2H), 1.38 (m, 4H), 1.11 (m, 1H). the reaction temperature below 10° C Wash the organic layer with 0.5M hydrochloride and brine Dry over sodium sulfate filter concentrate stir for 3 days Pour onto water and ice extract with methylene chloride Dry over sodium sulfate filter concentrate

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Dissolve 2,4-dibromo-butyryl chloride (17.0 g, 64.3 mmol) in chloroform (3 ml) and add to a mixture of cyclohexylamine (7.65 g, 77.2 mmol) in chloroform (20 mL) and H2O (3 mL) at 0° C. Add sodium hydroxide (5.92 g, 147.9 mmol) slowly while keeping the reaction temperature below 10° C. Stir for 1 hour. Wash the organic layer with 0.5M hydrochloride and brine. Dry over sodium sulfate, filter, and concentrate. Place the residue in THF (200 mL) and cool to 0° C. Add sodium hydride (1.02 g, 42.6 mmol) and stir for two days. Add additional sodium hydride (1.02 g, 42.6 mmol) and stir for 3 days. Pour onto water and ice and extract with methylene chloride. Dry over sodium sulfate, filter, and concentrate to yield 6.36 g (34%) of the title compound: NMR (CDCl3) δ 4.41 (dd, 1H), 3.94 (m, 1H), 3.48 (m, 1H), 3.33 (m, 1H), 2.51 (m, 1H), 2.30 (m, 1H), 1.82 (m, 3H), 1.70 (m, 2H), 1.38 (m, 4H), 1.11 (m, 1H). the reaction temperature below 10° C Wash the organic layer with 0.5M hydrochloride and brine Dry over sodium sulfate filter concentrate stir for 3 days Pour onto water and ice extract with methylene chloride Dry over sodium sulfate filter concentrate