N/A

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: Sodium borohydride (170 mg, 4.50 mmol) was added to and dissolved in N,N-dimethylacetamide (1.5 mL) at room temperature, followed by addition of an N,N-dimethylacetamide solution (1.0 mL) of ethyl 1-chloro-2-fluoro-cyclopropane-1-carboxylate (hereinafter the compound will be referred to as “compound (1b)”) (cis/trans=95/5) (500 mg, 3.00 mmol). Cobalt chloride hexahydrate (3.6 mg, 0.015 mmol) was added to the resultant solution at the same temperature. After completion of addition, the resultant mixture was stirred at 40° C. for one hour. After completion of reaction, the whole reaction mixture was diluted with an HPLC mobile phase to 50 mL, to thereby yield a solution containing 381.3 mg (yield: 96%) of the title compound. Yield was determined by means of high performance liquid chromatography (HPLC) (the same shall apply hereinafter). After completion of addition After completion of reaction the whole reaction mixture was diluted with an HPLC mobile phase to 50 mL to thereby yield a solution

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

实验步骤: Sodium borohydride (170 mg, 4.50 mmol) was added to and dissolved in N,N-dimethylacetamide (1.5 mL) at room temperature, followed by addition of an N,N-dimethylacetamide solution (1.0 mL) of ethyl 1-chloro-2-fluoro-cyclopropane-1-carboxylate (hereinafter the compound will be referred to as “compound (1b)”) (cis/trans=95/5) (500 mg, 3.00 mmol). Cobalt chloride hexahydrate (3.6 mg, 0.015 mmol) was added to the resultant solution at the same temperature. After completion of addition, the resultant mixture was stirred at 40° C. for one hour. After completion of reaction, the whole reaction mixture was diluted with an HPLC mobile phase to 50 mL, to thereby yield a solution containing 381.3 mg (yield: 96%) of the title compound. Yield was determined by means of high performance liquid chromatography (HPLC) (the same shall apply hereinafter). After completion of addition After completion of reaction the whole reaction mixture was diluted with an HPLC mobile phase to 50 mL to thereby yield a solution

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: An internal glass tube was introduced into an autoclave and 0.5 g of ethyl 1-chloro-2-fluoro-1-cyclopropanecarboxylate (cis:trans=1.4:1), 0.5 ml of Raney nickel and 5 ml of ethanol were fed thereinto. Then 0.18 mg of 1,2-diaminoethane was further added and the mixture was stirred at room temperature under an elevated hydrogen gas atmosphere (10 kgf/cm2) for 48 hours. After the completion of the reaction, the catalyst was filtered off. Then the reaction mixture containing the title compound was analyzed by gas chromatography. As a result, it was found out that the reaction conversion rate was 95%, the yield was 81% and the cis:trans ratio was 0.3:1. After the completion of the reaction the catalyst was filtered off Then the reaction mixture containing the title compound

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

实验步骤: An internal glass tube was introduced into an autoclave and 0.5 g of ethyl 2-bromo-2-fluoro-1-cyclopropanecarboxylate (cis:trans=0.8:1), 0.5 ml of Raney nickel and 5 ml of ethanol were fed thereinto. Then 0.43 g of 1,2-diaminoethane was further added and the mixture was stirred at room temperature under a hydrogen gas atmosphere (1 kgf/cm2) for 24 hours. After the completion of the reaction, the catalyst was filtered off. Then the reaction mixture containing the title compound was analyzed by gas chromatography. As a result, it was found out that the reaction conversion rate was 100%, the yield was 78% and the cis:trans ratio was 0.8:1. After the completion of the reaction the catalyst was filtered off Then the reaction mixture containing the title compound

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

实验步骤: An internal glass tube was introduced into an autoclave and 211 mg of ethyl 2-bromo-2-fluoro-1-cyclopropanecarboxylate [obtained in accordance with the method of Bulletin of Faculty of Education, Wakayama University, 33, 33 (1984); cis:trans=0.8:1], 40 mg of 5% palladium-carbon (moisture content: 55% wet) and 8 ml of ethanol were fed thereinto. Then 90 mg of 1,2-diaminoethane was further added and the mixture was stirred at room temperature under an elevated hydrogen gas atmosphere (50 kgf/cm2) for 48 hours. After the completion of the reaction, the catalyst was filtered off. Then the reaction mixture containing the title compound was analyzed by gas chromatography. As a result, it was found out that the reaction conversion rate was 95%, the yield was 81% and the cis:trans ratio was 0.8:1. obtained in accordance with the method of Bulletin of Faculty of Education, Wakayama University, 33, 33 (1984) After the completion of the reaction the catalyst was filtered off Then the reaction mixture containing the title compound

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

实验步骤: An internal glass tube was introduced into an autoclave and 0.5 g of ethyl 2-chloro-2-fluoro-1-cyclopropanecarboxylate (cis:trans=1.4:1), 0.5 ml of Raney nickel and 5 ml of ethanol were fed thereinto. Then 0.54 g of 1,2-diaminoethane was further added and the mixture was stirred at room temperature under an elevated hydrogen gas atmosphere (50 kgf/cm2) for 24 hours. After the completion of the reaction, the catalyst was filtered off. Then the reaction mixture was analyzed by gas chromatography. As a result, it was found out that the reaction conversion rate was 100%, the yield was 88.9% and the cis:trans ratio was 1.4:1. The analytical data of the title compound are as follows. After the completion of the reaction the catalyst was filtered off

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

实验步骤: Sodium borohydride (170 mg, 4.50 mmol) was added to and dissolved in N,N-dimethylacetamide (1.5 mL) at room temperature, followed by addition of an N,N-dimethylacetamide solution (1.0 mL) of ethyl 1-chloro-2-fluoro-cyclopropane-1-carboxylate (hereinafter the compound will be referred to as “compound (1b)”) (cis/trans=95/5) (500 mg, 3.00 mmol). Cobalt chloride hexahydrate (3.6 mg, 0.015 mmol) was added to the resultant solution at the same temperature. After completion of addition, the resultant mixture was stirred at 40° C. for one hour. After completion of reaction, the whole reaction mixture was diluted with an HPLC mobile phase to 50 mL, to thereby yield a solution containing 381.3 mg (yield: 96%) of the title compound. Yield was determined by means of high performance liquid chromatography (HPLC) (the same shall apply hereinafter). After completion of addition After completion of reaction the whole reaction mixture was diluted with an HPLC mobile phase to 50 mL to thereby yield a solution