tert-butyl N-(2,4-dihydroxybutyl)carbamate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (2,4-Dihydroxy-butyl)-carbamic acid tert-butyl ester in dichloromethane (15 ml) was added triethylamine (1.96 ml). The reaction mixture was cooled to 0° C. and methanesulfonyl chloride (0.82 ml) was added drop wise. The mixture was stirred at 0° C. for 2 hours. The mixture was filtered and dichloromethane was added (200 ml). The mixture was washed with 0.2M hydrochloric acid (50 ml), water (30 ml) and 0.2M sodium carbonate (50 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated to give crude methanesulfonic acid 1-(tert-butoxycarbonylamino-methyl)-3-methanesulfonyloxy-propyl ester (1.24 g) which was used in the next step without further purification. The mixture was filtered dichloromethane was added (200 ml) The mixture was washed with 0.2M hydrochloric acid (50 ml), water (30 ml) and 0.2M sodium carbonate (50 ml) The organic phase was dried over anhydrous sodium sulfate concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (2,4-Dihydroxy-butyl)-carbamic acid tert-butyl ester in dichloromethane (15 ml) was added triethylamine (1.96 ml). The reaction mixture was cooled to 0° C. and methanesulfonyl chloride (0.82 ml) was added drop wise. The mixture was stirred at 0° C. for 2 hours. The mixture was filtered and dichloromethane was added (200 ml). The mixture was washed with 0.2M hydrochloric acid (50 ml), water (30 ml) and 0.2M sodium carbonate (50 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated to give crude methanesulfonic acid 1-(tert-butoxycarbonylamino-methyl)-3-methanesulfonyloxy-propyl ester (1.24 g) which was used in the next step without further purification. The mixture was filtered dichloromethane was added (200 ml) The mixture was washed with 0.2M hydrochloric acid (50 ml), water (30 ml) and 0.2M sodium carbonate (50 ml) The organic phase was dried over anhydrous sodium sulfate concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a borane tetrahydrofuran complex solution 1M in tetrahydrofuran (15 ml) was added at 0° C. under an atmosphere of argon a solution of 4-tert-butoxycarbonylamino-3-hydroxy-butyric acid (1.5 g) in tetrahydrofuran (35 ml). The reaction mixture was stirred at 0° C. for 3 hours. The reaction was quenched by drop wise addition of 10% acetic acid in methanol (30 ml). Ethyl acetate was added (250 ml) and the mixture was washed with 1M hydrochloric acid (60 ml) and 1M sodium hydrogenocarbonate (80 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated. The residue was purified over silica gel (ethyl acetate/methanol 9:1) to give (2,4-dihydroxy-butyl)-carbamic acid tert-butyl ester (0.83 g). The reaction was quenched by drop wise addition of 10% acetic acid in methanol (30 ml) Ethyl acetate was added (250 ml) the mixture was washed with 1M hydrochloric acid (60 ml) and 1M sodium hydrogenocarbonate (80 ml) The organic phase was dried over anhydrous sodium sulfate concentrated The residue was purified over silica gel (ethyl acetate/methanol 9:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a borane tetrahydrofuran complex solution 1M in tetrahydrofuran (15 ml) was added at 0° C. under an atmosphere of argon a solution of 4-tert-butoxycarbonylamino-3-hydroxy-butyric acid (1.5 g) in tetrahydrofuran (35 ml). The reaction mixture was stirred at 0° C. for 3 hours. The reaction was quenched by drop wise addition of 10% acetic acid in methanol (30 ml). Ethyl acetate was added (250 ml) and the mixture was washed with 1M hydrochloric acid (60 ml) and 1M sodium hydrogenocarbonate (80 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated. The residue was purified over silica gel (ethyl acetate/methanol 9:1) to give (2,4-dihydroxy-butyl)-carbamic acid tert-butyl ester (0.83 g). The reaction was quenched by drop wise addition of 10% acetic acid in methanol (30 ml) Ethyl acetate was added (250 ml) the mixture was washed with 1M hydrochloric acid (60 ml) and 1M sodium hydrogenocarbonate (80 ml) The organic phase was dried over anhydrous sodium sulfate concentrated The residue was purified over silica gel (ethyl acetate/methanol 9:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (2,4-Dihydroxy-butyl)-carbamic acid tert-butyl ester in dichloromethane (15 ml) was added triethylamine (1.96 ml). The reaction mixture was cooled to 0° C. and methanesulfonyl chloride (0.82 ml) was added drop wise. The mixture was stirred at 0° C. for 2 hours. The mixture was filtered and dichloromethane was added (200 ml). The mixture was washed with 0.2M hydrochloric acid (50 ml), water (30 ml) and 0.2M sodium carbonate (50 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated to give crude methanesulfonic acid 1-(tert-butoxycarbonylamino-methyl)-3-methanesulfonyloxy-propyl ester (1.24 g) which was used in the next step without further purification. 1H-NMR (CDCl3, 400 MHz): 4.95 (m, 1H), 3.85 (m, 2H), 3.95 (m, 2H), 3.10 (m, 6H), 2.15 (m, 2H), 1.45 (s, 9H). The mixture was filtered dichloromethane was added (200 ml) The mixture was washed with 0.2M hydrochloric acid (50 ml), water (30 ml) and 0.2M sodium carbonate (50 ml) The organic phase was dried over anhydrous sodium sulfate concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (2,4-Dihydroxy-butyl)-carbamic acid tert-butyl ester in dichloromethane (15 ml) was added triethylamine (1.96 ml). The reaction mixture was cooled to 0° C. and methanesulfonyl chloride (0.82 ml) was added drop wise. The mixture was stirred at 0° C. for 2 hours. The mixture was filtered and dichloromethane was added (200 ml). The mixture was washed with 0.2M hydrochloric acid (50 ml), water (30 ml) and 0.2M sodium carbonate (50 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated to give crude methanesulfonic acid 1-(tert-butoxycarbonylamino-methyl)-3-methanesulfonyloxy-propyl ester (1.24 g) which was used in the next step without further purification. The mixture was filtered dichloromethane was added (200 ml) The mixture was washed with 0.2M hydrochloric acid (50 ml), water (30 ml) and 0.2M sodium carbonate (50 ml) The organic phase was dried over anhydrous sodium sulfate concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a borane tetrahydrofuran complex solution 1M in tetrahydrofuran (15 ml) was added at 0° C. under an atmosphere of argon a solution of 4-tert-butoxycarbonylamino-3-hydroxy-butyric acid (1.5 g) in tetrahydrofuran (35 ml). The reaction mixture was stirred at 0° C. for 3 hours. The reaction was quenched by drop wise addition of 10% acetic acid in methanol (30 ml). Ethyl acetate was added (250 ml) and the mixture was washed with 1M hydrochloric acid (60 ml) and 1M sodium hydrogenocarbonate (80 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated. The residue was purified over silica gel (ethyl acetate/methanol 9:1) to give (2,4-dihydroxy-butyl)-carbamic acid tert-butyl ester (0.83 g). The reaction was quenched by drop wise addition of 10% acetic acid in methanol (30 ml) Ethyl acetate was added (250 ml) the mixture was washed with 1M hydrochloric acid (60 ml) and 1M sodium hydrogenocarbonate (80 ml) The organic phase was dried over anhydrous sodium sulfate concentrated The residue was purified over silica gel (ethyl acetate/methanol 9:1)