(3S)-4-chloro-3-trimethylsilyloxybutanenitrile

Conditions: temp:27.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Mixture of zinc dust (69 grams) and methane sulfonic acid (6 ml) in tetrahydrofuran (500 ml) was heated to reflux temperature and stirred for an hour. (S)-4-chloro-3-(trimethylsilyloxy)butanenitrile (100 grams) followed by ethyl bromo acetate (147.2 grams) was added to the reaction mixture at 65-70° C. and stirred. After completion of the reaction, the reaction mixture was cooled to 25-30° C. and then added to the aqueous hydrochloric acid solution at 0° C. and stirred. The reaction mixture extracted into ethyl acetate and then washed it with sodium bicarbonate solution followed by sodium chloride solution. Ethyl acetate was distilled off from the reaction mixture under reduced pressure to get the title compound. was heated to reflux temperature was added to the reaction mixture at 65-70° C. stirred After completion of the reaction stirred The reaction mixture extracted into ethyl acetate washed it with sodium bicarbonate solution Ethyl acetate was distilled off from the reaction mixture under reduced pressure

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

Procedure: Zinc dust (690 mg), tetrahydrofuran (4.0 mL), and methanesulfonic acid (10 mg) were introduced into a reaction vessel and the mixture was stirred under reflux. To the mixture was added (S)-4-chloro-3-trimethylsilanyloxybutyronitrile (1.00 g) and subsequently t-butylbromoacetate (2.04 g) over 1 hour. The mixture was stirred under reflux for 30 minutes, and cooled to 0° C. Aqueous 3 N hydrochloric acid solution was added dropwise until the acidity of the reaction solution became pH 4, and the reaction solution was stirred for 3 hours. After the completion of reaction, tetrahydrofuran was distilled off under reduced pressure, and the residue was extracted with ethyl acetate and purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=⅓, v/v) to give the title compound in a yield of 87% (1.07 g). under reflux The mixture was stirred under reflux for 30 minutes the reaction solution was stirred for 3 hours was distilled off under reduced pressure the residue was extracted with ethyl acetate purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=⅓, v/v)

Conditions: temp:27.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Mixture of zinc dust (69 grams) and methane sulfonic acid (6 ml) in tetrahydrofuran (500 ml) was heated to reflux temperature and stirred for an hour. (S)-4-chloro-3-(trimethylsilyloxy)butanenitrile (100 grams) followed by ethyl bromo acetate (147.2 grams) was added to the reaction mixture at 65-70° C. and stirred. After completion of the reaction, the reaction mixture was cooled to 25-30° C. and then added to the aqueous hydrochloric acid solution at 0° C. and stirred. The reaction mixture extracted into ethyl acetate and then washed it with sodium bicarbonate solution followed by sodium chloride solution. Ethyl acetate was distilled off from the reaction mixture under reduced pressure to get the title compound. was heated to reflux temperature was added to the reaction mixture at 65-70° C. stirred After completion of the reaction stirred The reaction mixture extracted into ethyl acetate washed it with sodium bicarbonate solution Ethyl acetate was distilled off from the reaction mixture under reduced pressure