tert-butyl N-(2-hydroxyethyl)-N-propan-2-ylcarbamate

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(N-tert-butoxycarbonyl-N-isopropylamino)-ethanol (3.00 g, 14.8 mmol) and benzyl bromide (2.6 ml, 22.1 mmol) in anhydrous tetrahydrofuran (30 ml) was added to a solution of 60% sodium hydride (885 mg, 22.1 mmol) in anhydrous tetrahydrofuran (20 ml) under ice-cooling, and the mixture was stirred at 60° C. for four hours. Water (100 ml) was added to the reaction mixture under ice-cooling, the temperature was returned to room temperature, and the whole was extracted with ethyl acetate (100 ml). The organic layer was washed with saturated brine (100 ml) and dehydrated with anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure, and the obtained oily matter was purified by silica gel column chromatography (mobile phase:hexane/ethyl acetate=4/1) to give 1.30 g (30%) of the target compound. cooling cooling was returned to room temperature the whole was extracted with ethyl acetate (100 ml) The organic layer was washed with saturated brine (100 ml) Ethyl acetate was evaporated under reduced pressure the obtained oily matter was purified by silica gel column chromatography (mobile phase:hexane/ethyl acetate=4/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of dibutyl dicarbonate (25.0 g, 116 mmol) in tetrahydrofuran (40 ml) was added to a solution of 2-(isopropylamino)ethanol (10.0 g, 96.9 mmol) in tetrahydrofuran (60 ml) under ice-cooling. The mixture was stirred at room temperature for 3.5 hours, then a 10% aqueous citric acid solution (500 ml) was added to the reaction mixture, and the whole was extracted with ethyl acetate (500 ml). The organic layer was washed with saturated brine (500 ml) and dehydrated with anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure, and the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=1/1) to give 24.0 g (quantitatively) of the target compound. cooling the whole was extracted with ethyl acetate (500 ml) The organic layer was washed with saturated brine (500 ml) Ethyl acetate was evaporated under reduced pressure the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=1/1) to give 24.0 g (quantitatively) of the target compound

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(N-tert-butoxycarbonyl-N-isopropylamino)-ethanol (3.00 g, 14.8 mmol) and benzyl bromide (2.6 ml, 22.1 mmol) in anhydrous tetrahydrofuran (30 ml) was added to a solution of 60% sodium hydride (885 mg, 22.1 mmol) in anhydrous tetrahydrofuran (20 ml) under ice-cooling, and the mixture was stirred at 60° C. for four hours. Water (100 ml) was added to the reaction mixture under ice-cooling, the temperature was returned to room temperature, and the whole was extracted with ethyl acetate (100 ml). The organic layer was washed with saturated brine (100 ml) and dehydrated with anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure, and the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=4/1) to give 1.30 g (30%) of the target compound. cooling cooling was returned to room temperature the whole was extracted with ethyl acetate (100 ml) The organic layer was washed with saturated brine (100 ml) Ethyl acetate was evaporated under reduced pressure the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=4/1)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(N-tert-butoxycarbonyl-N-isopropylamino)-ethanol (3.00 g, 14.8 mmol) and benzyl bromide (2.6 ml, 22.1 mmol) in anhydrous tetrahydrofuran (30 ml) was added to a solution of 60% sodium hydride (885 mg, 22.1 mmol) in anhydrous tetrahydrofuran (20 ml) under ice-cooling, and the mixture was stirred at 60° C. for four hours. Water (100 ml) was added to the reaction mixture under ice-cooling, the temperature was returned to room temperature, and the whole was extracted with ethyl acetate (100 ml). The organic layer was washed with saturated brine (100 ml) and dehydrated with anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure, and the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=4/1) to give 1.30 g (30%) of the target compound. cooling cooling was returned to room temperature the whole was extracted with ethyl acetate (100 ml) The organic layer was washed with saturated brine (100 ml) Ethyl acetate was evaporated under reduced pressure the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=4/1)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(N-tert-butoxycarbonyl-N-isopropylamino)-ethanol (3.00 g, 14.8 mmol) and benzyl bromide (2.6 ml, 22.1 mmol) in anhydrous tetrahydrofuran (30 ml) was added to a solution of 60% sodium hydride (885 mg, 22.1 mmol) in anhydrous tetrahydrofuran (20 ml) under ice-cooling, and the mixture was stirred at 60° C. for four hours. Water (100 ml) was added to the reaction mixture under ice-cooling, the temperature was returned to room temperature, and the whole was extracted with ethyl acetate (100 ml). The organic layer was washed with saturated brine (100 ml) and dehydrated with anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure, and the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=4/1) to give 1.30 g (30%) of the target compound. cooling cooling was returned to room temperature the whole was extracted with ethyl acetate (100 ml) The organic layer was washed with saturated brine (100 ml) Ethyl acetate was evaporated under reduced pressure the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=4/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of dibutyl dicarbonate (25.0 g, 116 mmol) in tetrahydrofuran (40 ml) was added to a solution of 2-(isopropylamino)ethanol (10.0 g, 96.9 mmol) in tetrahydrofuran (60 ml) under ice-cooling. The mixture was stirred at room temperature for 3.5 hours, then a 10% aqueous citric acid solution (500 ml) was added to the reaction mixture, and the whole was extracted with ethyl acetate (500 ml). The organic layer was washed with saturated brine (500 ml) and dehydrated with anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure, and the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=1/1) to give 24.0 g (quantitatively) of the target compound. cooling the whole was extracted with ethyl acetate (500 ml) The organic layer was washed with saturated brine (500 ml) Ethyl acetate was evaporated under reduced pressure the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=1/1) to give 24.0 g (quantitatively) of the target compound

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of dibutyl dicarbonate (25.0 g, 116 mmol) in tetrahydrofuran (40 ml) was added to a solution of 2-(isopropylamino)ethanol (10.0 g, 96.9 mmol) in tetrahydrofuran (60 ml) under ice-cooling. The mixture was stirred at room temperature for 3.5 hours, then a 10% aqueous citric acid solution (500 ml) was added to the reaction mixture, and the whole was extracted with ethyl acetate (500 ml). The organic layer was washed with saturated brine (500 ml) and dehydrated with anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure, and the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=1/1) to give 24.0 g (quantitatively) of the target compound. cooling the whole was extracted with ethyl acetate (500 ml) The organic layer was washed with saturated brine (500 ml) Ethyl acetate was evaporated under reduced pressure the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=1/1) to give 24.0 g (quantitatively) of the target compound

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of dibutyl dicarbonate (25.0 g, 116 mmol) in tetrahydrofuran (40 ml) was added to a solution of 2-(isopropylamino)ethanol (10.0 g, 96.9 mmol) in tetrahydrofuran (60 ml) under ice-cooling. The mixture was stirred at room temperature for 3.5 hours, then a 10% aqueous citric acid solution (500 ml) was added to the reaction mixture, and the whole was extracted with ethyl acetate (500 ml). The organic layer was washed with saturated brine (500 ml) and dehydrated with anhydrous magnesium sulfate. Ethyl acetate was evaporated under reduced pressure, and the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=1/1) to give 24.0 g (quantitatively) of the target compound. cooling the whole was extracted with ethyl acetate (500 ml) The organic layer was washed with saturated brine (500 ml) Ethyl acetate was evaporated under reduced pressure the obtained oily matter was purified by silica gel column chromatography (mobile phase: hexane/ethyl acetate=1/1) to give 24.0 g (quantitatively) of the target compound

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Reaction of (2-hydroxyethyl)isopropylcarbamic acid tert-butyl ester with N-hydroxyphthalimide following the procedure described for Reference Example 14, except purification by column chromatography (silica gel, 75:25 hexanes/EtOAc to 50:50 hexanes/EtOAc), gave tert-butyl[2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]ethyl]isopropylcarbamate (960 mg, 57%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 1.15-1.20 (6H, br s), 1.43 (9H, s), 3.48-3.50 (2H, s), 4.08-4.15 (1H, m), 4.25-4.28 (2H, m), 7.74-7.85 (4H m). described for Reference Example 14, except purification by column chromatography (silica gel, 75:25 hexanes/EtOAc to 50:50 hexanes/EtOAc)