1-苯乙基-2-吡咯烷酮

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(2-phenylethyl)-2-pyrrolidinone (500 mg, 2.64 mmol) and THF (6 mL) is cooled to -78° C. Some precipitation occurred and 2 mL of THF is added. A solution of lithium diisopropylamide (LDA, 1.4 mL, 2.8 mmol, 2.0M in heptane/THF/ethylbenzene) is added and the mixture stirred at -78° C. for 40 minutes, giving a dark brown solution. To this solution is added 1-iodo-2-methylpropane (0.37 mL, 3.2 mmol). The solution is allowed to warm from -78° C. to 5° C. over 2.5 hours. After quenching with saturated aqueous ammonium chloride, aqueous workup (EtOAc, MgSO4) and purification by column chromatography (20% EtOAc/hexane) to give 642 mg (99%) of the title compound as a white solid (mp 69°-71° C.). Some precipitation 2 mL of THF is added giving a dark brown solution to warm from -78° C. to 5° C. over 2.5 hours After quenching with saturated aqueous ammonium chloride, aqueous workup (EtOAc, MgSO4) and purification by column chromatography (20% EtOAc/hexane)

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(2-phenylethyl)-2-pyrrolidinone (500 mg, 2.64 mmol) and THF (6 mL) is cooled to -78° C. Some precipitation occurred and 2 mL of THF is added. A solution of lithium diisopropylamide (LDA, 1.4 mL, 2.8 mmol, 2.0M in heptane/THF/ethylbenzene) is added and the mixture stirred at -78° C. for 40 minutes, giving a dark brown solution. To this solution is added 1-iodo-2-methylpropane (0.37 mL, 3.2 mmol). The solution is allowed to warm from -78° C. to 5° C. over 2.5 hours. After quenching with saturated aqueous ammonium chloride, aqueous workup (EtOAc, MgSO4) and purification by column chromatography (20% EtOAc/hexane) to give 642 mg (99%) of the title compound as a white solid (mp 69°-71° C.). Some precipitation 2 mL of THF is added giving a dark brown solution to warm from -78° C. to 5° C. over 2.5 hours After quenching with saturated aqueous ammonium chloride, aqueous workup (EtOAc, MgSO4) and purification by column chromatography (20% EtOAc/hexane)

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a stirring solution of HJC-1-53 (500 mg, 2.6 mmol), water (1 mL), 95% sulfuric acid (285 mg, 2.9 mmol) and acetic acid (8 mL) was added iodine (335 mg, 1.3 mmol) and periodic acid (H5IO6, 150 mg, 0.7 mmol) at rt. The reaction mixture was warmed to 60° C. for 3 h. After cooling down to rt, the solution was extracted with EtOAc (80 mL) and H2O (20 mL), and washed with 10% NaHSO3 (20 mL), followed by 10% NaHCO3 (40 mL). The organic layer was separated and washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give an oil residue. This residue was purified with silica gel column (Hexane/EtOAc=1/2) to obtain HJC-1-60 (130 mg, 16%) as a pale yellow oil. 1H NMR (600 MHz, CDCl3) δ 7.60 (d, 1H, J=7.8 Hz), 7.26-7.30 (m, 1H), 7.19-7.21 (m, 1H), 6.96 (d, 1H, J=9.0 Hz), 3.48-3.53 (m, 2H), 3.23-3.26 (m, 2H), 2.83 (t, 1H, J=7.8 Hz), 2.78 (t, 1H, J=7.8 Hz), 2.32-2.36 (m, 2H), 1.91-1.97 (m, 2H). After cooling down to rt the solution was extracted with EtOAc (80 mL) and H2O (20 mL) washed with 10% NaHSO3 (20 mL) The organic layer was separated washed with brine (10 mL) dried over anhydrous Na2SO4 filtered concentrated to give an oil residue This residue was purified with silica gel column (Hexane/EtOAc=1/2) to obtain HJC-1-60 (130 mg, 16%) as a pale yellow oil

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of HJC-1-48 (4.2 g, 18.6 mmol) in DCM/H2O (20 mL/8 mL) was added (n-Bu)4NBr (0.3 g, 0.9 mmol) and NaOH (3.7 g, 93.0 mmol). The resulting mixture was stirred at 100° C. for 7 h. The mixture was partitioned between EtOAc (200 mL) and H2O (10 mL). The organic layer was separated and washed with brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated to give an oil residue. This residue was purified with silica gel column (Hexane/EtOAc=1/1 to 1/2) to obtain HJC-1-53 (4.2 g, 93%) as a pale yellow oil. 1H NMR (600 MHz, CDCl3) δ 7.26-7.30 (m, 2H), 7.18-7.22 (m, 3H), 3.53 (t, 2H, J=7.8 Hz), 3.25 (t, 2H, J=7.2 Hz), 2.84 (t, 2H, J=7.8 Hz), 2.34 (t, 2H, J=7.8 Hz), 1.92-1.97 (m, 2H). The mixture was partitioned between EtOAc (200 mL) and H2O (10 mL) The organic layer was separated washed with brine (20 mL) dried over anhydrous Na2SO4 filtered concentrated to give an oil residue This residue was purified with silica gel column (Hexane/EtOAc=1/1 to 1/2) to obtain HJC-1-53 (4.2 g, 93%) as a pale yellow oil

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of HJC-1-48 (4.2 g, 18.6 mmol) in DCM/H2O (20 mL/8 mL) was added (n-Bu)4NBr (0.3 g, 0.9 mmol) and NaOH (3.7 g, 93.0 mmol). The resulting mixture was stirred at 100° C. for 7 h. The mixture was partitioned between EtOAc (200 mL) and H2O (10 mL). The organic layer was separated and washed with brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated to give an oil residue. This residue was purified with silica gel column (Hexane/EtOAc=1/1 to 1/2) to obtain HJC-1-53 (4.2 g, 93%) as a pale yellow oil. 1H NMR (600 MHz, CDCl3) δ 7.26-7.30 (m, 2H), 7.18-7.22 (m, 3H), 3.53 (t, 2H, J=7.8 Hz), 3.25 (t, 2H, J=7.2 Hz), 2.84 (t, 2H, J=7.8 Hz), 2.34 (t, 2H, J=7.8 Hz), 1.92-1.97 (m, 2H). The mixture was partitioned between EtOAc (200 mL) and H2O (10 mL) The organic layer was separated washed with brine (20 mL) dried over anhydrous Na2SO4 filtered concentrated to give an oil residue This residue was purified with silica gel column (Hexane/EtOAc=1/1 to 1/2) to obtain HJC-1-53 (4.2 g, 93%) as a pale yellow oil

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1-(2-phenylethyl)-2-pyrrolidinone (500 mg, 2.64 mmol) and THF (6 mL) is cooled to -78° C. Some precipitation occurred and 2 mL of THF is added. A solution of lithium diisopropylamide (LDA, 1.4 mL, 2.8 mmol, 2.0M in heptane/THF/ethylbenzene) is added and the mixture stirred at -78° C. for 40 minutes, giving a dark brown solution. To this solution is added 1-iodo-2-methylpropane (0.37 mL, 3.2 mmol). The solution is allowed to warm from -78° C. to 5° C. over 2.5 hours. After quenching with saturated aqueous ammonium chloride, aqueous workup (EtOAc, MgSO4) and purification by column chromatography (20% EtOAc/hexane) to give 642 mg (99%) of the title compound as a white solid (mp 69°-71° C.). Some precipitation 2 mL of THF is added giving a dark brown solution to warm from -78° C. to 5° C. over 2.5 hours After quenching with saturated aqueous ammonium chloride, aqueous workup (EtOAc, MgSO4) and purification by column chromatography (20% EtOAc/hexane)

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a stirring solution of HJC-1-53 (500 mg, 2.6 mmol), water (1 mL), 95% sulfuric acid (285 mg, 2.9 mmol) and acetic acid (8 mL) was added iodine (335 mg, 1.3 mmol) and periodic acid (H5IO6, 150 mg, 0.7 mmol) at rt. The reaction mixture was warmed to 60° C. for 3 h. After cooling down to rt, the solution was extracted with EtOAc (80 mL) and H2O (20 mL), and washed with 10% NaHSO3 (20 mL), followed by 10% NaHCO3 (40 mL). The organic layer was separated and washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give an oil residue. This residue was purified with silica gel column (Hexane/EtOAc=1/2) to obtain HJC-1-60 (130 mg, 16%) as a pale yellow oil. 1H NMR (600 MHz, CDCl3) δ 7.60 (d, 1H, J=7.8 Hz), 7.26-7.30 (m, 1H), 7.19-7.21 (m, 1H), 6.96 (d, 1H, J=9.0 Hz), 3.48-3.53 (m, 2H), 3.23-3.26 (m, 2H), 2.83 (t, 1H, J=7.8 Hz), 2.78 (t, 1H, J=7.8 Hz), 2.32-2.36 (m, 2H), 1.91-1.97 (m, 2H). After cooling down to rt the solution was extracted with EtOAc (80 mL) and H2O (20 mL) washed with 10% NaHSO3 (20 mL) The organic layer was separated washed with brine (10 mL) dried over anhydrous Na2SO4 filtered concentrated to give an oil residue This residue was purified with silica gel column (Hexane/EtOAc=1/2) to obtain HJC-1-60 (130 mg, 16%) as a pale yellow oil

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of HJC-1-48 (4.2 g, 18.6 mmol) in DCM/H2O (20 mL/8 mL) was added (n-Bu)4NBr (0.3 g, 0.9 mmol) and NaOH (3.7 g, 93.0 mmol). The resulting mixture was stirred at 100° C. for 7 h. The mixture was partitioned between EtOAc (200 mL) and H2O (10 mL). The organic layer was separated and washed with brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated to give an oil residue. This residue was purified with silica gel column (Hexane/EtOAc=1/1 to 1/2) to obtain HJC-1-53 (4.2 g, 93%) as a pale yellow oil. 1H NMR (600 MHz, CDCl3) δ 7.26-7.30 (m, 2H), 7.18-7.22 (m, 3H), 3.53 (t, 2H, J=7.8 Hz), 3.25 (t, 2H, J=7.2 Hz), 2.84 (t, 2H, J=7.8 Hz), 2.34 (t, 2H, J=7.8 Hz), 1.92-1.97 (m, 2H). The mixture was partitioned between EtOAc (200 mL) and H2O (10 mL) The organic layer was separated washed with brine (20 mL) dried over anhydrous Na2SO4 filtered concentrated to give an oil residue This residue was purified with silica gel column (Hexane/EtOAc=1/1 to 1/2) to obtain HJC-1-53 (4.2 g, 93%) as a pale yellow oil