tert-butyl N,N-bis(2-hydroxyethyl)carbamate

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

Procedure: To a solution of tert-butyl bis(2-hydroxyethyl)carbamate (8.20 g, 40 mmol) in hexane (30 mL) was added a solution of NaOH (8.00 g, 200 mmol) in water (30 mL), 1-bromopropane (9.84 g, 80 mmol) and TBAB (1.00 g) under N2. The reaction mixture was refluxed overnight, then cooled to rt and poured into CH2Cl2 (100 mL). The organic phase was washed with water (100 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as colorless oil (1.78 g, 15%). The reaction mixture was refluxed overnight The organic phase was washed with water (100 mL×3) dried over anhydrous Na2SO4 concentrated in vacuo The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

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

Procedure: In a dichloromethane/N,N-dimethylformamide (70 ml/70 ml) mixture were dissolved t-butyl N,N-bis(2-hydroxyethyl)carbamate (9.00 g, 43.8 mmol) and imidazole (2.60 g, 38.2 mmol), followed by the dropwise addition of t-butylchlorodiphenylsilane (8.1 ml, 31 mmol) at room temperature. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 14 hours. The residue obtained by concentrating the reaction mixture under reduced pressure was added with diethyl ether. The resulting mixture was washed with water and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=2:1 eluate was concentrated under reduced pressure, whereby the title compound (7.41 g, 16.7 mmol, 54%) was obtained as a colorless oil. After completion of the dropwise addition The residue obtained by concentrating the reaction mixture under reduced pressure was added with diethyl ether The resulting mixture was washed with water the organic layer was dried over anhydrous magnesium sulfate After filtration the filtrate was concentrated under reduced pressure The residue thus obtained

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

Procedure: In a dichloromethane/N,N-dimethylformamide (70 ml/70 ml) mixture were dissolved t-butyl N,N-bis(2-hydroxyethyl)carbamate (9.00 g, 43.8 mmol) and imidazole (2.60 g, 38.2 mmol), followed by the dropwise addition of t-butylchlorodiphenylsilane (8.1 ml, 31 mmol) at room temperature. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 14 hours. The residue obtained by concentrating the reaction mixture under reduced pressure was added with diethyl ether. The resulting mixture was washed with water and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=2:1 eluate was concentrated under reduced pressure, whereby the title compound (7.41 g, 16.7 mmol, 54%) was obtained as a colorless oil. After completion of the dropwise addition The residue obtained by concentrating the reaction mixture under reduced pressure was added with diethyl ether The resulting mixture was washed with water the organic layer was dried over anhydrous magnesium sulfate After filtration the filtrate was concentrated under reduced pressure The residue thus obtained

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

Procedure: To a solution of tert-butyl bis(2-hydroxyethyl)carbamate (8.20 g, 40 mmol) in hexane (30 mL) was added a solution of NaOH (8.00 g, 200 mmol) in water (30 mL), 1-bromopropane (9.84 g, 80 mmol) and TBAB (1.00 g) under N2. The reaction mixture was refluxed overnight, then cooled to rt and poured into CH2Cl2 (100 mL). The organic phase was washed with water (100 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as colorless oil (1.78 g, 15%). The reaction mixture was refluxed overnight The organic phase was washed with water (100 mL×3) dried over anhydrous Na2SO4 concentrated in vacuo The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

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

Procedure: To a solution of tert-butyl bis(2-hydroxyethyl)carbamate (8.20 g, 40 mmol) in hexane (30 mL) was added a solution of NaOH (8.00 g, 200 mmol) in water (30 mL), 1-bromopropane (9.84 g, 80 mmol) and TBAB (1.00 g) under N2. The reaction mixture was refluxed overnight, then cooled to rt and poured into CH2Cl2 (100 mL). The organic phase was washed with water (100 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as colorless oil (1.78 g, 15%). The reaction mixture was refluxed overnight The organic phase was washed with water (100 mL×3) dried over anhydrous Na2SO4 concentrated in vacuo The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1)

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

Procedure: The procedure of Example 1 was followed using N-boc diethanolamine (3 g, 14.6 mmol), triethylamine (4.1 mL, 29.2 mmol), dry dichloromethane (100 mL) and triphosgene (1.4 g, 4.9 mmol). The filtrate was concentrated yielding only oligomeric compounds. The filtrate was concentrated yielding only oligomeric compounds

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

Procedure: tert-Butyl bis(2-hydroxyethyl)carbamate (Aldrich; 600 mg, 2.92 mmol) was dissolved in dichloromethane (30 mL), and stirred overnight at room temperature after adding oleic acid (Tokyo Chemical Industry Co., Ltd.; 1.82 g, 6.43 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.29 g, 6.72 mmol), and 4-dimethylaminopyridine (89 mg, 0.731 mmol). The aqueous layer was extracted with ethyl acetate after adding a saturated sodium bicarbonate aqueous solution to the reaction mixture. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure after filtration. The resulting residue was purified by silica gel column chromatography (hexane/chloroform=50/50 to 0/100) to give tert-butyl N,N-bis(2-((Z)-octadec-9-enoyloxy)ethyl)carbamate (1.26 g, 58.7%). The aqueous layer was extracted with ethyl acetate after adding a saturated sodium bicarbonate aqueous solution to the reaction mixture The organic layer was washed with saturated brine dried over magnesium sulfate concentrated under reduced pressure after filtration The resulting residue was purified by silica gel column chromatography (hexane/chloroform=50/50 to 0/100)

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

Procedure: In a dichloromethane/N,N-dimethylformamide (70 ml/70 ml) mixture were dissolved t-butyl N,N-bis(2-hydroxyethyl)carbamate (9.00 g, 43.8 mmol) and imidazole (2.60 g, 38.2 mmol), followed by the dropwise addition of t-butylchlorodiphenylsilane (8.1 ml, 31 mmol) at room temperature. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 14 hours. The residue obtained by concentrating the reaction mixture under reduced pressure was added with diethyl ether. The resulting mixture was washed with water and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=2:1 eluate was concentrated under reduced pressure, whereby the title compound (7.41 g, 16.7 mmol, 54%) was obtained as a colorless oil. After completion of the dropwise addition The residue obtained by concentrating the reaction mixture under reduced pressure was added with diethyl ether The resulting mixture was washed with water the organic layer was dried over anhydrous magnesium sulfate After filtration the filtrate was concentrated under reduced pressure The residue thus obtained