5-bromo-2-methylpentan-2-ol

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

実験手順: To a −50° C. cooled solution of alcohol 8 (3 g, 16.6 mmol) in anhydrous CH2Cl2 (50 mL) was added 2,6-lutidine (2.32 mL, 2.13 g, 19.89 mmol) followed by TBSOTf (4.57 mL, 5.26 g, 19.9 mmol). The solution was stirred at 0° C. for 15 min and water (10 mL) was added. The mixture was extracted with CH2Cl2 (3×40 mL), and combined organic phases were washed with 1N aqueous solution of NaOH (40 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane) to give 3.9 g (13.2 mmol, 80%) of 9. 1H NMR (400 MHz, CDCl3) δ: 0.07 (6H, s), 0.85 (9H, s), 1.21 (6H, s), 1.55 (2H, m), 1.95 (2H, m),3.41 (2H, t, J=6.8 Hz) The mixture was extracted with CH2Cl2 (3×40 mL) were washed with 1N aqueous solution of NaOH (40 mL) dried (Na2SO4) filtered concentrated The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane)

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

実験手順: To a −50° C. cooled solution of alcohol 8 (3 g, 16.6 mmol) in anhydrous CH2Cl2 (50 mL) was added 2,6-lutidine (2.32 mL, 2.13 g, 19.89 mmol) followed by TBSOTf (4.57 mL, 5.26 g, 19.9 mmol). The solution was stirred at 0° C. for 15 min and water (10 mL) was added. The mixture was extracted with CH2Cl2 (3×40 mL), and combined organic phases were washed with 1N aqueous solution of NaOH (40 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane) to give 3.9 g (13.2 mmol, 80%) of 9. 1H NMR (400 MHz, CDCl3) δ: 0.07 (6H, s), 0.85 (9H, s), 1.21 (6H, s), 1.55 (2H, m), 1.95 (2H, m),3.41 (2H, t, J=6.8 Hz) The mixture was extracted with CH2Cl2 (3×40 mL) were washed with 1N aqueous solution of NaOH (40 mL) dried (Na2SO4) filtered concentrated The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane)

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.1 g, 0.23 mmol) was dissolved in DMF (5 mL) at room temperature. K2CO3 (0.317 g, 2.3 mmol) was added. 5-Bromo-2-methyl-pentan-2-ol (0.092 g, 0.51 mmol) was added and the reaction was allowed to heat to 80° C. overnight. The reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water, then extracted three times with ethyl acetate, dried over MgSO4, filtered and concentrated down. The crude residue was purified by silica gel chromatography (70% EtOAc/30% Hexane) to afford the product (0.097 g, 79%). The reaction mixture was concentrated in vacuo The residue was partitioned between ethyl acetate and water extracted three times with ethyl acetate dried over MgSO4 filtered concentrated down The crude residue was purified by silica gel chromatography (70% EtOAc/30% Hexane)

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

実験手順: To a −50° C. cooled solution of alcohol 8 (3 g, 16.6 mmol) in anhydrous CH2Cl2 (50 mL) was added 2,6-lutidine (2.32 mL, 2.13 g, 19.89 mmol) followed by TBSOTf (4.57 mL, 5.26 g, 19.9 mmol). The solution was stirred at 0° C. for 15 min and water (10 mL) was added. The mixture was extracted with CH2Cl2 (3×40 mL), and combined organic phases were washed with 1N aqueous solution of NaOH (40 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane) to give 3.9 g (13.2 mmol, 80%) of 9. 1H NMR (400 MHz, CDCl3) δ: 0.07 (6H, s), 0.85 (9H, s), 1.21 (6H, s), 1.55 (2H, m), 1.95 (2H, m), 3.41 (2H, t, J=6.8 Hz) The mixture was extracted with CH2Cl2 (3×40 mL) were washed with 1N aqueous solution of NaOH (40 mL) dried (Na2SO4) filtered concentrated The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane)

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

実験手順: To a −50° C. cooled solution of alcohol 8 (3 g, 16.6 mmol) in anhydrous CH2Cl2 (50 mL) was added 2,6-lutidine (2.32 mL, 2.13 g, 19.89 mmol) followed by TBSOTf (4.57 mL, 5.26 g, 19.9 mmol). The solution was stirred at 0° C. for 15 min and water (10 mL) was added. The mixture was extracted with CH2Cl2 (3×40 mL), and combined organic phases were washed with 1N aqueous solution of NaOH (40 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (5% ethyl acetate/hexane) to give 3.9 g (13.2 mmol, 80%) of 9. 1H NMR (400 MHz, CDCl3) δ: 0.07 (6H, s), 0.85 (9H, s), 1.21 (6H, s), 1.55 (2H, m), 1.95 (2H, m), 3.41 (2H, t, J=6.8 Hz) The mixture was extracted with CH2Cl2 (3×40 mL) were washed with 1N aqueous solution of NaOH (40 mL) dried (Na2SO4) filtered concentrated The residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)

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

実験手順: To a −50° C. cooled solution of alcohol 8 (3 g, 16.6 mmol) in anhydrous CH2Cl2 (50 mL) was added 2,6-lutidine (2.32 mL, 2.13 g, 19.89 mmol) followed by TBSOTf (4.57 mL, 5.26 g, 19.9 mmol). The solution was stirred at 0° C. for 15 min and water (10 mL) was added. The mixture was extracted with CH2Cl2 (3×40 mL), and combined organic phases were washed with IN aqueous solution of NaOH (40 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (5% ethyl acetate/hexane) to give 3.9 g (13.2 mmol, 80%) of 9. H NMR (400 MHz, CDCl3) δ: 0.07 (6H, s), 0.85 (9H, s), 1.21 (6H, s), 1.55 (2H, m), 1.95 (2H, m), 3.41 (2H, t, J=6.8 Hz) The mixture was extracted with CH2Cl2 (3×40 mL) were washed with IN aqueous solution of NaOH (40 mL) dried (Na2SO4) filtered concentrated The residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)

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

実験手順: To a −50° C. cooled solution of alcohol 8 (3 g, 16.6 mmol) in anhydrous CH2Cl2 (50 mL) was added 2,6-lutidine (2.32 mL, 2.13 g, 19.89 mmol) followed by TBSOTf (4.57 mL, 5.26 g, 19.9 mmol). The solution was stirred at 0° C. for 15 min and water (10 mL) was added. The mixture was extracted with CH2Cl2 (3×40 mL), and combined organic phases were washed with 1N aqueous solution of NaOH (40 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane) to give 3.9 g (13.2 mmol, 80%) of 9. 1H NMR (400 MHz, CDCl3) δ: 0.07 (6H, s), 0.85 (9H, s), 1.21 (6H, s), 1.55 (2H, m), 1.95 (2H, m), 3.41 (2H, t, J=6.8 Hz) The mixture was extracted with CH2Cl2 (3×40 mL) were washed with 1N aqueous solution of NaOH (40 mL) dried (Na2SO4) filtered concentrated The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane)

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

実験手順: To a −50° C. cooled solution of alcohol 8 (3 g, 16.6 mmol) in anhydrous CH2Cl2 (50 mL) was added 2,6-lutidine (2.32 mL, 2.13 g, 19.89 mmol) followed by TBSOTf (4.57 mL, 5.26 g, 19.9 mmol). The solution was stirred at 0° C. for 15 min and water (10 mL) was added. The mixture was extracted with CH2Cl2 (3×40 mL), and combined organic phases were washed with 1N aqueous solution of NaOH (40 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane) to give 3.9 g (13.2 mmol, 80%) of 9. 1H NMR (400 MHz, CDCl3) δ: 0.07 (6H, s), 0.85 (9H, s), 1.21 (6H, s), 1.55 (2H, m), 1.95 (2H, m), 3.41 (2H, t, J=6.8 Hz) The mixture was extracted with CH2Cl2 (3×40 mL) were washed with 1N aqueous solution of NaOH (40 mL) dried (Na2SO4) filtered concentrated The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane)

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

実験手順: To a −50° C. cooled solution of alcohol 8 (3 g, 16.6 mmol) in anhydrous CH2Cl2 (50 mL) was added 2,6-lutidine (2.32 mL, 2.13 g, 19.89 mmol) followed by TBSOTf (4.57 mL, 5.26 g, 19.9 mmol). The solution was stirred at 0° C. for 15 min and water (10 mL) was added. The mixture was extracted with CH2Cl2 (3×40 mL), and combined organic phases were washed with 1N aqueous solution of NaOH (40 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane) to give 3.9 g (13.2 mmol, 80%) of 9. 1H NMR (400 MHz, CDCl3) δ: 0.07 (6H, s), 0.85 (9H, s), 1.21 (6H, s), 1.55 (2H, m), 1.95 (2H, m),3.41 (2H, t, J=6.8 Hz) The mixture was extracted with CH2Cl2 (3×40 mL) were washed with 1N aqueous solution of NaOH (40 mL) dried (Na2SO4) filtered concentrated The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane)