1-(propylamino)propan-2-ol

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

実験手順: To a solution of 1-(propylamino)propan-2-ol (8.00 g, 68.3 mmol), tert-butylchlorodimethylsilane (10.9 g, 72.4 mmol), and catalytic amount of DMAP in CH2Cl2 (68 mL) at 0° C. was added dropwise TEA (9.61 ml, 68.3 mmol). The reaction mixture was warmed to room temperature and stirred for 20 h. Additional 1 mL of TEA was added and stirred for additional 20 h. Water (60 mL) was added. The layers were separated. The aqueous layer was extracted with EtOAc (1×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was filtered again to afford quantitatively 2-(tert-butyldimethylsilyloxy)-N-propylpropan-1-amine that was used directly without further purification. stirred for additional 20 h The layers were separated The aqueous layer was extracted with EtOAc (1×) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated under reduced pressure to give the crude material that was filtered again

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

実験手順: To a solution of 1-(propylamino)propan-2-ol (8.00 g, 68.3 mmol), tert-butylchlorodimethylsilane (10.9 g, 72.4 mmol), and catalytic amount of DMAP in CH2Cl2 (68 mL) at 0° C. was added dropwise TEA (9.61 ml, 68.3 mmol). The reaction mixture was warmed to room temperature and stirred for 20 h. Additional 1 mL of TEA was added and stirred for additional 20 h. Water (60 mL) was added. The layers were separated. The aqueous layer was extracted with EtOAc (1×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was filtered again to afford quantitatively 2-(tert-butyldimethylsilyloxy)-N-propylpropan-1-amine that was used directly without further purification. stirred for additional 20 h The layers were separated The aqueous layer was extracted with EtOAc (1×) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated under reduced pressure to give the crude material that was filtered again

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

実験手順: To a solution of 1-(propylamino)propan-2-ol (8.00 g, 68.3 mmol), tert-butylchlorodimethylsilane (10.9 g, 72.4 mmol), and catalytic amount of DMAP in CH2Cl2 (68 mL) at 0° C. was added dropwise TEA (9.61 ml, 68.3 mmol). The reaction mixture was warmed to room temperature and stirred for 20 h. Additional 1 mL of TEA was added and stirred for additional 20 h. Water (60 mL) was added. The layers were separated. The aqueous layer was extracted with EtOAc (1×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was filtered again to afford quantitatively 2-(tert-butyldimethylsilyloxy)-N-propylpropan-1-amine that was used directly without further purification. stirred for additional 20 h The layers were separated The aqueous layer was extracted with EtOAc (1×) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated under reduced pressure to give the crude material that was filtered again

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

実験手順: To a solution of 1-(propylamino)propan-2-ol (8.00 g, 68.3 mmol), tert-butylchlorodimethylsilane (10.9 g, 72.4 mmol), and catalytic amount of DMAP in CH2Cl2 (68 mL) at 0° C. was added dropwise TEA (9.61 ml, 68.3 mmol). The reaction mixture was warmed to room temperature and stirred for 20 h. Additional 1 mL of TEA was added and stirred for additional 20 h. Water (60 mL) was added. The layers were separated. The aqueous layer was extracted with EtOAc (1×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was filtered again to afford quantitatively 2-(tert-butyldimethylsilyloxy)-N-propylpropan-1-amine that was used directly without further purification. stirred for additional 20 h The layers were separated The aqueous layer was extracted with EtOAc (1×) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated under reduced pressure to give the crude material that was filtered again

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

実験手順: To a solution of 1-(propylamino)propan-2-ol (8.00 g, 68.3 mmol), tert-butylchlorodimethylsilane (10.9 g, 72.4 mmol), and catalytic amount of DMAP in CH2Cl2 (68 mL) at 0° C. was added dropwise TEA (9.61 ml, 68.3 mmol). The reaction mixture was warmed to room temperature and stirred for 20 h. Additional 1 mL of TEA was added and stirred for additional 20 h. Water (60 mL) was added. The layers were separated. The aqueous layer was extracted with EtOAc (1×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was filtered again to afford quantitatively 2-(tert-butyldimethylsilyloxy)-N-propylpropan-1-amine that was used directly without further purification. stirred for additional 20 h The layers were separated The aqueous layer was extracted with EtOAc (1×) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated under reduced pressure to give the crude material that was filtered again

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

実験手順: 17.43 g (0.100 mol) of 1,3-bis-(propylamino-propan-2-ol was mixed with 110 ml (0.220 mol) of 2N caustic soda solution and stirred at room temperature for 10 minutes. The mixture was cooled to 0° C. A solution of 19.46 g (0.215 mol) of acrylic acid chloride and 20 mg of BHT in 120 ml of chloroform was added dropwise at 0° C. within 3 hours 30 minutes. After the addition was completed the reaction mixture was stirred at 0° C. for 2 hours 30 minutes. Organic and aqueous phases were separated. The aqueous phase was saturated with NaCl and extracted with 5×80 ml of methylene chloride. The combined organic phases were dried over Na2SO4, filtered, concentrated in a rotary evaporator after addition of 20 mg of BHT and dried in a fine vacuum. The raw product was purified by means of two-fold column chromatography (silica gel 60, 0.035-0.070 mm, ethyl acetate). 11.92 g (42.2 mmol; 42%) of the pure product was obtained as a yellowish oil. The mixture was cooled to 0° C After the addition was stirred at 0° C. for 2 hours 30 minutes Organic and aqueous phases were separated extracted with 5×80 ml of methylene chloride The combined organic phases were dried over Na2SO4 filtered concentrated in a rotary evaporator after addition of 20 mg of BHT dried in a fine vacuum The raw product was purified by means of two-fold column chromatography (silica gel 60, 0.035-0.070 mm, ethyl acetate) 11.92 g (42.2 mmol; 42%) of the pure product was obtained as a yellowish oil

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

実験手順: To a solution of 1-(propylamino)propan-2-ol (8.00 g, 68.3 mmol), tert-butylchlorodimethylsilane (10.9 g, 72.4 mmol), and catalytic amount of DMAP in CH2Cl2 (68 mL) at 0° C. was added dropwise TEA (9.61 ml, 68.3 mmol). The reaction mixture was warmed to room temperature and stirred for 20 h. Additional 1 mL of TEA was added and stirred for additional 20 h. Water (60 mL) was added. The layers were separated. The aqueous layer was extracted with EtOAc (1×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was filtered again to afford quantitatively 2-(tert-butyldimethylsilyloxy)-N-propylpropan-1-amine that was used directly without further purification. stirred for additional 20 h The layers were separated The aqueous layer was extracted with EtOAc (1×) The combined organic layers were washed with brine dried over MgSO4 filtered concentrated under reduced pressure to give the crude material that was filtered again