(S)-3,4-Dihydroxybutyronitrile

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

Procedure: (3S)-3,4-Dihydroxybutyronitrile (16.2 g, 160 mmol) was dissolved in pyridine (26.0 ml). To the resulting solution, a solution of mesyl chloride (14.8 ml) in methylene chloride (160 ml) was added at 0° C. and stirred at 0° C. for 6 hours. Then, the pH of the mixture was adjusted at 2 with 6N hydrochloric acid, and the mixture was extracted with methylene chloride. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off. The residue was purified with silica gel column chromatography (acetone:chloroform=5:95) to obtain (3S)-3-hydroxy-4-methanesulfonyloxybutyronitrile (15.2 g). Yield, 53 %. the mixture was extracted with methylene chloride After the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated off The residue was purified with silica gel column chromatography (acetone:chloroform=5:95)

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

Procedure: (3S)-3,4-Dihydroxybutyronitrile (8.0 g, 79.1 mmol), pyridine (19.1 ml) and mesyl chloride (7.33 ml) were mixed at 0° C. for 6 hours. The mixture was poured in ice-cooled 1N hydrochloric acid and stirred, followed by extraction with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off with an evaporator. The residue was purified with silica gel column chromatography (acetone:chloroform=5:95) to obtain (3S)-3-hydroxy-4-methanesulfonyloxybutyronitrile (8.1 g). Yield, 57 %. The mixture was poured in ice- followed by extraction with ethyl acetate After the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated off with an evaporator The residue was purified with silica gel column chromatography (acetone:chloroform=5:95)

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

Procedure: (3S)-3,4-Dihydroxybutyronitrile (8.0 g, 79.1 mmol), pyridine (19.1 ml) and mesyl chloride (7.33 ml) were mixed at 0° C. for 6 hours. The mixture was poured in ice-cooled 1N hydrochloric acid and stirred, followed by extraction with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off with an evaporator. The residue was purified with silica gel column chromatography (acetone:chloroform=5:95) to obtain (3S)-3-hydroxy-4-methanesulfonyloxybutyronitrile (8.1 g). Yield, 57 %. The mixture was poured in ice- followed by extraction with ethyl acetate After the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated off with an evaporator The residue was purified with silica gel column chromatography (acetone:chloroform=5:95)

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

Procedure: (3S)-3,4-Dihydroxybutyronitrile (161.8 g, 1.6 mol) was dissolved in pyridine (260 ml). To the resulting solution, a solution of tosyl chloride (396.6 g) in methylene chloride (1.6 liters) was added at 0° C. and stirred at 0° C. for 5 hours. Then, the pH of the mixture was adjusted at 2 with 6N hydrochloric acid, and the mixture was extracted with methylene chloride. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain (3S)-3-hydroxy-4-p-toluenesulfonyloxybutyronitrile (85.9 g). Yield, 70 %. the mixture was extracted with methylene chloride After the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated off The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1)

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

Procedure: (3S)-3,4-Dihydroxybutyronitrile (43.1 g, 426 mmol), pyridine (240 ml) and tosyl chloride (119.5 g) were mixed at 0° C. for 4 hours. The mixture was poured in ice-cooled 1N hydrochloric acid and stirred, followed by extraction with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off with an evaporator. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain (3S)-3-hydroxy-4-p-toluenesulfonyloxybutyronitrile (87.0 g, 340 mmol). Yield, 80 %. The mixture was poured in ice- followed by extraction with ethyl acetate After the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated off with an evaporator The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1)

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

Procedure: (3S)-3,4-Dihydroxybutyronitrile (43.1 g, 426 mmol), pyridine (240 ml) and tosyl chloride (119.5 g) were mixed at 0° C. for 4 hours. The mixture was poured in ice-cooled 1N hydrochloric acid and stirred, followed by extraction with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off with an evaporator. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain (3S)-3-hydroxy-4-p-toluenesulfonyloxybutyronitrile (87.0 g, 340 mmol). Yield, 80 %. The mixture was poured in ice- followed by extraction with ethyl acetate After the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated off with an evaporator The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1)

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

Procedure: (3S)-3,4-Dihydroxybutyronitrile (16.2 g, 160 mmol) was dissolved in pyridine (26.0 ml). To the resulting solution, a solution of mesyl chloride (14.8 ml) in methylene chloride (160 ml) was added at 0° C. and stirred at 0° C. for 6 hours. Then, the pH of the mixture was adjusted at 2 with 6N hydrochloric acid, and the mixture was extracted with methylene chloride. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off. The residue was purified with silica gel column chromatography (acetone:chloroform=5:95) to obtain (3S)-3-hydroxy-4-methanesulfonyloxybutyronitrile (15.2 g). Yield, 53 %. the mixture was extracted with methylene chloride After the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated off The residue was purified with silica gel column chromatography (acetone:chloroform=5:95)

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

Procedure: (3S)-3,4-Dihydroxybutyronitrile (8.0 g, 79.1 mmol), pyridine (19.1 ml) and mesyl chloride (7.33 ml) were mixed at 0° C. for 6 hours. The mixture was poured in ice-cooled 1N hydrochloric acid and stirred, followed by extraction with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off with an evaporator. The residue was purified with silica gel column chromatography (acetone:chloroform=5:95) to obtain (3S)-3-hydroxy-4-methanesulfonyloxybutyronitrile (8.1 g). Yield, 57 %. The mixture was poured in ice- followed by extraction with ethyl acetate After the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated off with an evaporator The residue was purified with silica gel column chromatography (acetone:chloroform=5:95)

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

Procedure: (3S)-3,4-Dihydroxybutyronitrile (161.8 g, 1.6 mol) was dissolved in pyridine (260 ml). To the resulting solution, a solution of tosyl chloride (396.6 g) in methylene chloride (1.6 liters) was added at 0° C. and stirred at 0° C. for 5 hours. Then, the pH of the mixture was adjusted at 2 with 6N hydrochloric acid, and the mixture was extracted with methylene chloride. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain (3S)-3-hydroxy-4-p-toluenesulfonyloxybutyronitrile (85.9 g). Yield, 70 %. the mixture was extracted with methylene chloride After the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated off The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1)

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

Procedure: (3S)-3,4-Dihydroxybutyronitrile (43.1 g, 426 mmol), pyridine (240 ml) and tosyl chloride (119.5 g) were mixed at 0° C. for 4 hours. The mixture was poured in ice-cooled 1N hydrochloric acid and stirred, followed by extraction with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off with an evaporator. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain (3S)-3-hydroxy-4-p-toluenesulfonyloxybutyronitrile (87.0 g, 340 mmol). Yield, 80 %. The mixture was poured in ice- followed by extraction with ethyl acetate After the organic layer was dried over anhydrous sodium sulfate the solvent was evaporated off with an evaporator The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1)