L-4-甲基苯丙氨醇

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A stirred solution of (2S)-2-amino-3-(4-methylphenyl)propan-1-ol (Step A, 460 mg, 2.79 mmol) in CH2Cl2 (20 mL) at 0° C. was treated with diisopropylethylamine (2.92 mL, 16.74 mmol) and triphosgene (414 mg, 1.39 mmol) under an atmosphere of N2. The reaction stirred at 0° C. for 3 h. The reaction was quenched with sat. NaHCO3 (10 mL) and extracted with EtOAc (4×20 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash silica gel chromatography (0-70% EtOAc/hexanes gradient) to afford (4S)-4-(4-methylbenzyl)-1,3-oxazolidin-2-one as a white solid. LCMS=192.2 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.17 (d, J=8 Hz, 2 H), 7.09 (d, J=7.7 Hz, 2 H), 5.39 (br s, 1 H), 4.48 (t, J=8.4 Hz, 1 H), 4.37 (dd, J=8.6, 5.6 Hz, 1 H), 4.11-4.06 (m, 1 H), 2.86 (d, J=7.1 Hz, 2 H), 2.36 (s, 3 H). The reaction was quenched with sat. NaHCO3 (10 mL) extracted with EtOAc (4×20 mL) The combined organic layers were washed with brine (25 mL) dried (MgSO4) filtered concentrated in vacuo The crude product was purified by flash silica gel chromatography (0-70% EtOAc/hexanes gradient)

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A stirred solution of (2S)-2-amino-3-(4-methylphenyl)propan-1-ol (Step A, 460 mg, 2.79 mmol) in CH2Cl2 (20 mL) at 0° C. was treated with diisopropylethylamine (2.92 mL, 16.74 mmol) and triphosgene (414 mg, 1.39 mmol) under an atmosphere of N2. The reaction stirred at 0° C. for 3 h. The reaction was quenched with sat. NaHCO3 (10 mL) and extracted with EtOAc (4×20 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash silica gel chromatography (0-70% EtOAc/hexanes gradient) to afford (4S)-4-(4-methylbenzyl)-1,3-oxazolidin-2-one as a white solid. LCMS=192.2 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.17 (d, J=8 Hz, 2 H), 7.09 (d, J=7.7 Hz, 2 H), 5.39 (br s, 1 H), 4.48 (t, J=8.4 Hz, 1 H), 4.37 (dd, J=8.6, 5.6 Hz, 1 H), 4.11-4.06 (m, 1 H), 2.86 (d, J=7.1 Hz, 2 H), 2.36 (s, 3 H). The reaction was quenched with sat. NaHCO3 (10 mL) extracted with EtOAc (4×20 mL) The combined organic layers were washed with brine (25 mL) dried (MgSO4) filtered concentrated in vacuo The crude product was purified by flash silica gel chromatography (0-70% EtOAc/hexanes gradient)

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

实验步骤: A mixture of lithium aluminum hydride (254 mg, 6.696 mmol) in THF (20 mL) was heated at reflux for 1 h, then cooled in an ice bath. (S)-4-Methylphenylalanine (500 mg, 2.79 mmol) was added portionwise and the resultant mixture was heated at reflux for 14 h. The excess lithium aluminum hydride was decomposed by successive addition of H2O (1 mL), 10% aq. NaOH (10 mL) and H2O (2.5 mL). The mixture was filtered and the solid was washed with THF. The filtrate was concentrated in vacuo and the residue was dissolved in CHCl3 (50 mL), washed with 5% aq. NaOH (25 mL), H2O (25 mL) and brine (25 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford (2S)-2-amino-3-(4-methylphenyl)propan-1-ol as an off-white solid. 1H NMR (CD3OD, 500 MHz) δ 7.13-7.09 (m, 4H), 3.52 (dd, J=10.7, 4.6 Hz, 1H), 3.36 (dd, J=10.7, 6.9 Hz, 1H), 3.04-2.99 (m, 1 H), 2.73 (dd, J=13.5, 6.2 Hz, 1H), 2.53 (dd, J=13.5, 7.7 Hz, 1H), 2.30 (s, 3 H). was heated at reflux for 1 h cooled in an ice bath at reflux for 14 h The mixture was filtered the solid was washed with THF The filtrate was concentrated in vacuo the residue was dissolved in CHCl3 (50 mL) washed with 5% aq. NaOH (25 mL), H2O (25 mL) and brine (25 mL) dried (MgSO4) filtered concentrated in vacuo

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

实验步骤: A mixture of lithium aluminum hydride (254 mg, 6.696 mmol) in THF (20 mL) was heated at reflux for 1 h, then cooled in an ice bath. (S)-4-Methylphenylalanine (500 mg, 2.79 mmol) was added portionwise and the resultant mixture was heated at reflux for 14 h. The excess lithium aluminum hydride was decomposed by successive addition of H2O (1 mL), 10% aq. NaOH (10 mL) and H2O (2.5 mL). The mixture was filtered and the solid was washed with THF. The filtrate was concentrated in vacuo and the residue was dissolved in CHCl3 (50 mL), washed with 5% aq. NaOH (25 mL), H2O (25 mL) and brine (25 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford (2S)-2-amino-3-(4-methylphenyl)propan-1-ol as an off-white solid. 1H NMR (CD3OD, 500 MHz) δ 7.13-7.09 (m, 4H), 3.52 (dd, J=10.7, 4.6 Hz, 1H), 3.36 (dd, J=10.7, 6.9 Hz, 1H), 3.04-2.99 (m, 1H), 2.73 (dd, J=13.5, 6.2 Hz, 1H), 2.53 (dd, J=13.5, 7.7 Hz, 1H), 2.30 (s, 3H). was heated at reflux for 1 h cooled in an ice bath at reflux for 14 h The mixture was filtered the solid was washed with THF The filtrate was concentrated in vacuo the residue was dissolved in CHCl3 (50 mL) washed with 5% aq. NaOH (25 mL), H2O (25 mL) and brine (25 mL) dried (MgSO4) filtered concentrated in vacuo

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A stirred solution of (2S)-2-amino-3-(4-methylphenyl)propan-1-ol (Step A, 460 mg, 2.79 mmol) in CH2Cl2 (20 mL) at 0° C. was treated with diisopropylethylamine (2.92 mL, 16.74 mmol) and triphosgene (414 mg, 1.39 mmol) under an atmosphere of N2. The reaction stirred at 0° C. for 3 h. The reaction was quenched with sat. NaHCO3 (10 mL) and extracted with EtOAc (4×20 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash silica gel chromatography (0-70% EtOAc/hexanes gradient) to afford (4S)-4-(4-methylbenzyl)-1,3-oxazolidin-2-one as a white solid. LCMS=192.2 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.17 (d, J=8 Hz, 2H), 7.09 (d, J=7.7 Hz, 2H), 5.39 (br s, 1H), 4.48 (t, J=8.4 Hz, 1H), 4.37 (dd, J=8.6, 5.6 Hz, 1H), 4.11-4.06 (m, 1H), 2.86 (d, J=7.1 Hz, 2H), 2.36 (s, 3H). The reaction was quenched with sat. NaHCO3 (10 mL) extracted with EtOAc (4×20 mL) The combined organic layers were washed with brine (25 mL) dried (MgSO4) filtered concentrated in vacuo The crude product was purified by flash silica gel chromatography (0-70% EtOAc/hexanes gradient)

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A stirred solution of (2S)-2-amino-3-(4-methylphenyl)propan-1-ol (Step A, 460 mg, 2.79 mmol) in CH2Cl2 (20 mL) at 0° C. was treated with diisopropylethylamine (2.92 mL, 16.74 mmol) and triphosgene (414 mg, 1.39 mmol) under an atmosphere of N2. The reaction stirred at 0° C. for 3 h. The reaction was quenched with sat. NaHCO3 (10 mL) and extracted with EtOAc (4×20 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash silica gel chromatography (0-70% EtOAc/hexanes gradient) to afford (4S)-4-(4-methylbenzyl)-1,3-oxazolidin-2-one as a white solid. LCMS=192.2 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.17 (d, J=8 Hz, 2 H), 7.09 (d, J=7.7 Hz, 2 H), 5.39 (br s, 1 H), 4.48 (t, J=8.4 Hz, 1 H), 4.37 (dd, J=8.6, 5.6 Hz, 1 H), 4.11-4.06 (m, 1 H), 2.86 (d, J=7.1 Hz, 2 H), 2.36 (s, 3 H). The reaction was quenched with sat. NaHCO3 (10 mL) extracted with EtOAc (4×20 mL) The combined organic layers were washed with brine (25 mL) dried (MgSO4) filtered concentrated in vacuo The crude product was purified by flash silica gel chromatography (0-70% EtOAc/hexanes gradient)

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

实验步骤: A mixture of lithium aluminum hydride (254 mg, 6.696 mmol) in THF (20 mL) was heated at reflux for 1 h, then cooled in an ice bath. (S)-4-Methylphenylalanine (500 mg, 2.79 mmol) was added portionwise and the resultant mixture was heated at reflux for 14 h. The excess lithium aluminum hydride was decomposed by successive addition of H2O (1 mL), 10% aq. NaOH (10 mL) and H2O (2.5 mL). The mixture was filtered and the solid was washed with THF. The filtrate was concentrated in vacuo and the residue was dissolved in CHCl3 (50 mL), washed with 5% aq. NaOH (25 mL), H2O (25 mL) and brine (25 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford (2S)-2-amino-3-(4-methylphenyl)propan-1-ol as an off-white solid. 1H NMR (CD3OD, 500 MHz) δ 7.13-7.09 (m, 4H), 3.52 (dd, J=10.7, 4.6 Hz, 1H), 3.36 (dd, J=10.7, 6.9 Hz, 1H), 3.04-2.99 (m, 1 H), 2.73 (dd, J=13.5, 6.2 Hz, 1H), 2.53 (dd, J=13.5, 7.7 Hz, 1H), 2.30 (s, 3 H). was heated at reflux for 1 h cooled in an ice bath at reflux for 14 h The mixture was filtered the solid was washed with THF The filtrate was concentrated in vacuo the residue was dissolved in CHCl3 (50 mL) washed with 5% aq. NaOH (25 mL), H2O (25 mL) and brine (25 mL) dried (MgSO4) filtered concentrated in vacuo