methyl aziridine-2-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a flame dried Schlenk tube equipped with a magnetic stirring bar, a rubber septum and a N2 inlet was added aziridine-2-carboxylic acid methyl ester 1d (1.01 g, 10 mmol) dissolved into 25 ml of anhydrous toluene. The reaction flask was cooled to −78° C., at which point 13 ml of a 1.5M solution of DIBAL in toluene was added slowly via syringe to the reaction mixture over a period of 30 minutes. The reaction was allowed to stir for 5 hours or until completed by TLC. MeOH was added via syringe to the reaction mixture over a period of 15 minutes while maintaining a temperature of −78° C. After the addition of MeOH, the reaction mixture was allowed to warm to room temperature and stir for 30 minutes. A few drops of saturated aqueous Na2SO4 were used to cause precipitation of aluminum salts, which were filtered off after stirring for another 30 minutes. The filtrate was concentrated under reduced pressure to yield a thick clear oil, which was pure enough by NMR to use in subsequent transformations. An analytically pure sample can be obtained by subjecting the crude product to flash column chromatography (silica gel; 20% water in MeCN, Rf=0.32) to yield the title compound as a colourless oil in 76% yield. The compound is water soluble. 1H NMR (CDCl3 with D2O present, 400 MHz) δ: 5.33 (s, 0.5H), 5.27 (s, 1H), 4.92 (s, 1H), 4.91 (s, 0.5H), 2.62 (dd, J=5.2 Hz, 3.2 Hz, 1H), 2.53 (dd, J=5.6 Hz, 3.6 Hz, 0.5H), 2.47-2.43 (m, 1H), 2.39 (quintet, J=3.2 Hz, 0.5H), 2.29 (d, J=3.6 Hz, 0.5H), 2.10 (d, J=6.4 Hz, 0.5H), 1.86 (d, J=6.4 Hz, 1H), 1.76 (d, J=5.2 Hz, 1H), 1.70 (dd, J=5.2 Hz, 3.6 Hz, 1.5H), 1.26 (d, J=3.2 Hz, 1H), 1.21 (d, J=3.2 Hz, 0.5H) ppm. 13C NMR (CDCl3, 100 MHz) δ: 96.6 (major), 95.7 (minor), 95.6 (minor), 94.8 (major), 44.8 (minor), 44.0 (major), 31.9 (minor), 31.6 (major), 28.0 (major), 27.6 (minor), 21.3 ppm. To a flame dried Schlenk tube equipped with a magnetic stirring bar was added slowly via syringe to the reaction mixture over a period of 30 minutes while maintaining a temperature of −78° C to warm to room temperature stir for 30 minutes precipitation of aluminum salts, which were filtered off after stirring for another 30 minutes The filtrate was concentrated under reduced pressure to yield a thick clear oil, which An analytically pure sample can be obtained

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a flame dried Schlenk tube equipped with a magnetic stirring bar, a rubber septum and a N2 inlet was added aziridine-2-carboxylic acid methyl ester 1d (1.01 g, 10 mmol) dissolved into 25 ml of anhydrous toluene. The reaction flask was cooled to −78° C., at which point 13 ml of a 1.5M solution of DIBAL in toluene was added slowly via syringe to the reaction mixture over a period of 30 minutes. The reaction was allowed to stir for 5 hours or until completed by TLC. MeOH was added via syringe to the reaction mixture over a period of 15 minutes while maintaining a temperature of −78° C. After the addition of MeOH, the reaction mixture was allowed to warm to room temperature and stir for 30 minutes. A few drops of saturated aqueous Na2SO4 were used to cause precipitation of aluminum salts, which were filtered off after stirring for another 30 minutes. The filtrate was concentrated under reduced pressure to yield a thick clear oil, which was pure enough by NMR to use in subsequent transformations. An analytically pure sample can be obtained by subjecting the crude product to flash column chromatography (silica gel; 20% water in MeCN, Rf=0.32) to yield the title compound as a colourless oil in 76% yield. The compound is water soluble. 1H NMR (CDCl3 with D2O present, 400 MHz) δ: 5.33 (s, 0.5H), 5.27 (s, 1H), 4.92 (s, 1H), 4.91 (s, 0.5H), 2.62 (dd, J=5.2 Hz, 3.2 Hz, 1H), 2.53 (dd, J=5.6 Hz, 3.6 Hz, 0.5H), 2.47-2.43 (m, 1H), 2.39 (quintet, J=3.2 Hz, 0.5H), 2.29 (d, J=3.6 Hz, 0.5H), 2.10 (d, J=6.4 Hz, 0.5H), 1.86 (d, J=6.4 Hz, 1H), 1.76 (d, J=5.2 Hz, 1H), 1.70 (dd, J=5.2 Hz, 3.6 Hz, 1.5H), 1.26 (d, J=3.2 Hz, 1H), 1.21 (d, J=3.2 Hz, 0.5H) ppm. 13C NMR (CDCl3, 100 MHz) δ: 96.6 (major), 95.7 (minor), 95.6 (minor), 94.8 (major), 44.8 (minor), 44.0 (major), 31.9 (minor), 31.6 (major), 28.0 (major), 27.6 (minor), 21.3 ppm. To a flame dried Schlenk tube equipped with a magnetic stirring bar was added slowly via syringe to the reaction mixture over a period of 30 minutes while maintaining a temperature of −78° C to warm to room temperature stir for 30 minutes precipitation of aluminum salts, which were filtered off after stirring for another 30 minutes The filtrate was concentrated under reduced pressure to yield a thick clear oil, which An analytically pure sample can be obtained

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 4.40 g (43.5 mmol) methyl aziridine-2-carboxylate and 13.5 ml (97.3 mmol) triethylamine in 30 ml methylene chloride is combined with 8.80 g (48.6 mmol) 5-chlorothiophenecarboxylic acid chloride in 30 ml methylene chloride while cooling with ice and subsequently after removal of the cooling bath stirred for 3 h at room temperature. Then the mixture is diluted with water, extracted with methylene chloride, dried with sodium sulphate, concentrated and purified by chromatography (silica gel, petroleum ether/ethyl acetate 80/15->80/20) to obtain the slightly contaminated title compound. while cooling with ice subsequently after removal of the cooling bath Then the mixture is diluted with water extracted with methylene chloride dried with sodium sulphate concentrated purified by chromatography (silica gel, petroleum ether/ethyl acetate 80/15->80/20)

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

Procedure: To a stirred solution of aziridine-2-carboxylic acid methyl ester (0.5 g) in dichloromethane (20 ml) at 0° C. were added triethylamine (0.95 g) and isopropylsulfonyl chloride (1.38 g). The mixture was warmed to room temperature and stirred for 3.5 h. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with brine. The organic phase was dried (MgSO4), filtered and evaporated to give the crude 1-(propane-2-sulfonyl)-aziridine-2-carboxylic acid methyl ester as a yellow oil. The mixture was filtered the filtrate was concentrated The residue was dissolved in ethyl acetate washed with brine The organic phase was dried (MgSO4) filtered evaporated

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a flame dried Schlenk tube equipped with a magnetic stirring bar, a rubber septum and a N2 inlet was added aziridine-2-carboxylic acid methyl ester 1d (1.01 g, 10 mmol) dissolved into 25 ml of anhydrous toluene. The reaction flask was cooled to −78° C., at which point 13 ml of a 1.5M solution of DIBAL in toluene was added slowly via syringe to the reaction mixture over a period of 30 minutes. The reaction was allowed to stir for 5 hours or until completed by TLC. MeOH was added via syringe to the reaction mixture over a period of 15 minutes while maintaining a temperature of −78° C. After the addition of MeOH, the reaction mixture was allowed to warm to room temperature and stir for 30 minutes. A few drops of saturated aqueous Na2SO4 were used to cause precipitation of aluminum salts, which were filtered off after stirring for another 30 minutes. The filtrate was concentrated under reduced pressure to yield a thick clear oil, which was pure enough by NMR to use in subsequent transformations. An analytically pure sample can be obtained by subjecting the crude product to flash column chromatography (silica gel; 20% water in MeCN, Rf=0.32) to yield the title compound as a colourless oil in 76% yield. The compound is water soluble. 1H NMR (CDCl3 with D2O present, 400 MHz) δ: 5.33 (s, 0.5H), 5.27 (s, 1H), 4.92 (s, 1H), 4.91 (s, 0.5H), 2.62 (dd, J=5.2 Hz, 3.2 Hz, 1H), 2.53 (dd, J=5.6 Hz, 3.6 Hz, 0.5H), 2.47-2.43 (m, 1H), 2.39 (quintet, J=3.2 Hz, 0.5H), 2.29 (d, J=3.6 Hz, 0.5H), 2.10 (d, J=6.4 Hz, 0.5H), 1.86 (d, J=6.4 Hz, 1H), 1.76 (d, J=5.2 Hz, 1H), 1.70 (dd, J=5.2 Hz, 3.6 Hz, 1.5H), 1.26 (d, J=3.2 Hz, 1H), 1.21 (d, J=3.2 Hz, 0.5H) ppm. 13C NMR (CDCl3, 100 MHz) δ: 96.6 (major), 95.7 (minor), 95.6 (minor), 94.8 (major), 44.8 (minor), 44.0 (major), 31.9 (minor), 31.6 (major), 28.0 (major), 27.6 (minor), 21.3 ppm. To a flame dried Schlenk tube equipped with a magnetic stirring bar was added slowly via syringe to the reaction mixture over a period of 30 minutes while maintaining a temperature of −78° C to warm to room temperature stir for 30 minutes precipitation of aluminum salts, which were filtered off after stirring for another 30 minutes The filtrate was concentrated under reduced pressure to yield a thick clear oil, which An analytically pure sample can be obtained