(S)-2-(二苯甲基氨基)丁烷-1-醇

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

实验步骤: A 2M solution of oxalyl chloride in dichloromethane (3.18 ml, 6.36 mmol) was cooled to −78 0° C. and diluted with dry dichloromethane (20 ml) under dry nitrogen. A solution of dimethylsulfoxide (1 g, 12.72 mmol) in anhydrous dichloromethane was added dropwise to the cooled stirred solution. The reaction was stirred for a further 1 h after completion of addition. A solution of (S)-2-(dibenzylamino) butan-1-ol (1.43 g, 5.3 mmol) in dichloromethane was added over 5 minutes. After 10 minutes, diisopropylethylamine (2.73 g, 21.2 mmol) was added. The reaction was allowed to warm to room temperature and left stiffing for 1 h. It was cooled to 0° C. and ethyl acetate/water (50 ml: 50 ml) was added. The organic layer was washed with water (50 ml), brine (50 ml) dried (MgSO4) and concentrated. The product was purified by flash silica column chromatography (ethyl acetate:Hexane 1: 4) to provide the pure product (1.28 g, 90.5%). δH (250 MHz, CDCl3) 0.88 (3 H, t, J 7.5, CHCH2CH3), 1.77-1.54 (2 H, m, CH2CH3), 2.99 (1 H, t,J 7.5, CHCH2CH3), 3.74-3.57 (4 H, m, 2×CH2Ph), 7.31-7.11 (10 H, m, 2×C6H5) 9.64 (1 H, s, CHO); δC (250 MHz, CDCl3) 203.9 (CO), 139.33 (2×C), 128.99 (4×CH), 128.45 (4×CH), 127.3 (2×CH), 68.46 (CH), 54.85 (CH2), 17.44 (CH2), 11.83 (CH3); m/z 268.2 (M+H) The reaction was stirred for a further 1 h after completion of addition left stiffing for 1 h It was cooled to 0° C. The organic layer was washed with water (50 ml), brine (50 ml) dried (MgSO4) concentrated The product was purified by flash silica column chromatography (ethyl acetate:Hexane 1: 4)

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

实验步骤: To a stirred solution of (S)-(+)-2-aminobutan-1-ol (5 g, 56.18 mmol) in dry acetonitrile (100 ml) was added dry powdered potassium carbonate (31 g, 224.72 mmol) followed by benzyl bromide (19 g, 111.11 mmol). The reaction was stirred at room temperature for 24 h. The solvent was removed under vacuo and the residue was taken up in ethyl acetate (100 ml) and water (100 ml). The organic phase was washed again with water, dried (Na2SO4) and concentrated to provide the pure product as slightly yellow oil (14.5 g, 97.3%). δH (250 MHz, CDCl3) 0.98 (3 H, t, J 7.5, CHCH2CH3), 1.38-1.2 (1 H, m, CHCHHCH3), 1.94-1.78 (1 H, m, CHHCH3), 2.83-2.71 (1 H, m, CHCHHCH3), 3.22 (1 H, s, b, OH), 3.65-3.4 (2 H, m, CH2OH), 3.47 (2 H, d, J 17.5, 2×CHHPh), 3.94 (2 H, d, J 17.5, 2×CHHPh), 7.46-7.26 (10 H, m, 2×C6H5); δC (250 MHz, CDCl3) 139.42 (2×C), 129.1 (2×CH), 128.52 (2×CH), 127.25 (2×CH), 61.97 (CH), 60.67 (CH2), 53.23 (CH2), 17.92 (CH2), 11.83 (CH3); m/z 270.2 (M+H) The solvent was removed under vacuo The organic phase was washed again with water dried (Na2SO4) concentrated

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

实验步骤: To a stirred solution of (S)-(+)-2-aminobutan-1-ol (5 g, 56.18 mmol) in dry acetonitrile (100 ml) was added dry powdered potassium carbonate (31 g, 224.72 mmol) followed by benzyl bromide (19 g, 111.11 mmol). The reaction was stirred at room temperature for 24 h. The solvent was removed under vacuo and the residue was taken up in ethyl acetate (100 ml) and water (100 ml). The organic phase was washed again with water, dried (Na2SO4) and concentrated to provide the pure product as slightly yellow oil (14.5 g, 97.3%). δH (250 MHz, CDCl3) 0.98 (3 H, t, J 7.5, CHCH2CH3), 1.38-1.2 (1 H, m, CHCHHCH3), 1.94-1.78 (1 H, m, CHHCH3), 2.83-2.71 (1 H, m, CHCHHCH3), 3.22 (1 H, s, b, OH), 3.65-3.4 (2 H, m, CH2OH), 3.47 (2 H, d, J 17.5, 2×CHHPh), 3.94 (2 H, d, J 17.5, 2×CHHPh), 7.46-7.26 (10 H, m, 2×C6H5); δC (250 MHz, CDCl3) 139.42 (2×C), 129.1 (2×CH), 128.52 (2×CH), 127.25 (2×CH), 61.97 (CH), 60.67 (CH2), 53.23 (CH2), 17.92 (CH2), 11.83 (CH3); m/z 270.2 (M+H) The solvent was removed under vacuo The organic phase was washed again with water dried (Na2SO4) concentrated

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

实验步骤: A 2M solution of oxalyl chloride in dichloromethane (3.18 ml, 6.36 mmol) was cooled to −78 0° C. and diluted with dry dichloromethane (20 ml) under dry nitrogen. A solution of dimethylsulfoxide (1 g, 12.72 mmol) in anhydrous dichloromethane was added dropwise to the cooled stirred solution. The reaction was stirred for a further 1 h after completion of addition. A solution of (S)-2-(dibenzylamino) butan-1-ol (1.43 g, 5.3 mmol) in dichloromethane was added over 5 minutes. After 10 minutes, diisopropylethylamine (2.73 g, 21.2 mmol) was added. The reaction was allowed to warm to room temperature and left stiffing for 1 h. It was cooled to 0° C. and ethyl acetate/water (50 ml: 50 ml) was added. The organic layer was washed with water (50 ml), brine (50 ml) dried (MgSO4) and concentrated. The product was purified by flash silica column chromatography (ethyl acetate:Hexane 1:4) to provide the pure product (1.28 g, 90.5%). δH (250 MHz, CDCl3) 0.88 (3 H, t, J 7.5, CHCH2CH3), 1.77-1.54 (2 H, m, CH2CH3), 2.99 (1 H, t, J 7.5, CHCH2CH3), 3.74-3.57 (4 H, m, 2×CH2Ph), 7.31-7.11 (10 H, m, 2×C6H5) 9.64 (1 H, s, CHO); δC (250 MHz, CDCl3) 203.9 (CO), 139.33 (2×C), 128.99 (4×CH), 128.45 (4×CH), 127.3 (2×CH), 68.46 (CH), 54.85 (CH2), 17.44 (CH2), 11.83 (CH3); m/z 268.2 (M+H) The reaction was stirred for a further 1 h after completion of addition left stiffing for 1 h It was cooled to 0° C. The organic layer was washed with water (50 ml), brine (50 ml) dried (MgSO4) concentrated The product was purified by flash silica column chromatography (ethyl acetate:Hexane 1:4)

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

实验步骤: To a stirred solution of (S)-(+)-2-aminobutan-1-ol (5 g, 56.18 mmol) in dry acetonitrile (100 ml) was added dry powdered potassium carbonate (31 g, 224.72 mmol) followed by benzyl bromide (19 g, 111.11 mmol). The reaction was stirred at room temperature for 24 h. The solvent was removed under vaccuo and the residue was taken up in ethyl acetate (100 ml) and water (100 ml). The organic phase was washed again with water, dried (Na2SO4) and concentrated to provide the pure product as slightly yellow oil (14.5 g, 97.3%). δH (250 MHz, CDCl3) 0.98 (3 H, t, J 7.5, CHCH2CH3), 1.38-1.2 (1H, m, CHCHHCH3), 1.94-1.78 (1 H, m, CHHCH3), 2.83-2.71 (1 H, m, CHCHHCH3), 3.22 (1 H, s, b, OH), 3.65-3.4 (2 H, m, CH2OH), 3.47 (2 H, d, J 17.5, 2×CHHPh), 3.94 (2H, d, J 17.5, 2×CHHPh), 7.46-7.26 (10 H, m, 2×C6H5); δC (250 MHz, CDCl3) 139.42 (2×C), 129.1 (2×CH), 128.52 (2×CH), 127.25 (2×CH), 61.97 (CH), 60.67 (CH2), 53.23 (CH2), 17.92 (CH2), 11.83 (CH3); m/z 270.2 (M+H) The solvent was removed under vaccuo The organic phase was washed again with water dried (Na2SO4) concentrated

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

实验步骤: A 2M solution of oxalyl chloride in dichloromethane (3.18 ml, 6.36 mmol) was cooled to −78 0° C. and diluted with dry dichloromethane (20 ml) under dry nitrogen. A solution of dimethylsulfoxide (1 g, 12.72 mmol) in anhydrous dichloromethane was added dropwise to the cooled stirred solution. The reaction was stirred for a further 1 h after completion of addition. A solution of (S)-2-(dibenzylamino) butan-1-ol (1.43 g, 5.3 mmol) in dichloromethane was added over 5 minutes. After 10 minutes, diisopropylethylamine (2.73 g, 21.2 mmol) was added. The reaction was allowed to warm to room temperature and left stiffing for 1 h. It was cooled to 0° C. and ethyl acetate/water (50 ml: 50 ml) was added. The organic layer was washed with water (50 ml), brine (50 ml) dried (MgSO4) and concentrated. The product was purified by flash silica column chromatography (ethyl acetate:Hexane 1: 4) to provide the pure product (1.28 g, 90.5%). δH (250 MHz, CDCl3) 0.88 (3 H, t, J 7.5, CHCH2CH3), 1.77-1.54 (2 H, m, CH2CH3), 2.99 (1 H, t,J 7.5, CHCH2CH3), 3.74-3.57 (4 H, m, 2×CH2Ph), 7.31-7.11 (10 H, m, 2×C6H5) 9.64 (1 H, s, CHO); δC (250 MHz, CDCl3) 203.9 (CO), 139.33 (2×C), 128.99 (4×CH), 128.45 (4×CH), 127.3 (2×CH), 68.46 (CH), 54.85 (CH2), 17.44 (CH2), 11.83 (CH3); m/z 268.2 (M+H) The reaction was stirred for a further 1 h after completion of addition left stiffing for 1 h It was cooled to 0° C. The organic layer was washed with water (50 ml), brine (50 ml) dried (MgSO4) concentrated The product was purified by flash silica column chromatography (ethyl acetate:Hexane 1: 4)

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

实验步骤: To a stirred solution of (S)-(+)-2-aminobutan-1-ol (5 g, 56.18 mmol) in dry acetonitrile (100 ml) was added dry powdered potassium carbonate (31 g, 224.72 mmol) followed by benzyl bromide (19 g, 111.11 mmol). The reaction was stirred at room temperature for 24 h. The solvent was removed under vacuo and the residue was taken up in ethyl acetate (100 ml) and water (100 ml). The organic phase was washed again with water, dried (Na2SO4) and concentrated to provide the pure product as slightly yellow oil (14.5 g, 97.3%). δH (250 MHz, CDCl3) 0.98 (3 H, t, J 7.5, CHCH2CH3), 1.38-1.2 (1 H, m, CHCHHCH3), 1.94-1.78 (1 H, m, CHHCH3), 2.83-2.71 (1 H, m, CHCHHCH3), 3.22 (1 H, s, b, OH), 3.65-3.4 (2 H, m, CH2OH), 3.47 (2 H, d, J 17.5, 2×CHHPh), 3.94 (2 H, d, J 17.5, 2×CHHPh), 7.46-7.26 (10 H, m, 2×C6H5); δC (250 MHz, CDCl3) 139.42 (2×C), 129.1 (2×CH), 128.52 (2×CH), 127.25 (2×CH), 61.97 (CH), 60.67 (CH2), 53.23 (CH2), 17.92 (CH2), 11.83 (CH3); m/z 270.2 (M+H) The solvent was removed under vacuo The organic phase was washed again with water dried (Na2SO4) concentrated