ethyl 4-chloro-3-hydroxybutanoate

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

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

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

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

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

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

Procedure: The resulting product was esterified with (R)α-methoxy-α-trifluoromethylphenylacetyl chloride, and the ester was analyzed by HPLC. From the area ratio of the chromatogram, the optical yield of the product was found to be 97.2% ee.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 200 ml-volume stainless steel-made autoclave whose atmosphere had been replaced with nitrogen were charged 8.23 g (50 mmoles) of ethyl 4-chloroacetoacetate and 20 ml of ethanol. To the mixture was added 84 mg (0.05 mmole) of Ru2Cl4 ((-)-BINAP)2 (C2H5)3N, and the mixture was heated to 100° C. When the temperature reached 100° C., 100 kg/cm2 of hydrogen was introduced into the autoclave, and the mixture was stirred under heating. After cooling to room temperature, the reaction mixture was taken out, and the ethanol was removed by distillation. Distillation of the residue gave 8.07 g (97) of ethyl 4-chloro-3-hydroxybutyrate having a boiling point of 74°-75° C./l mmHg). reached 100° C. under heating After cooling to room temperature the ethanol was removed by distillation Distillation of the residue

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

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

Procedure: In a 50 mL-volumetric autoclave was added deaerated ethanol (10 mL), and thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (S)-epichlorohydrin (1.9 g, 20 mmol, >99% ee). Then to the mixture was added crystalline dicobaltoctacarbonyl complex (171 mg, 0.5 mmol). After covering the autoclave with a cap, carbon monoxide (1 MPa) was introduced therein and the mixture was reacted at 30° C. for 30 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give 4-chloro-3-hydroxybutanoic acid ethyl ester (3.1 g, 92%, >99% ee) as a colorless oil. bp: 80° C./0.6 mmHg. was introduced the mixture was reacted at 30° C. for 30 hours the solvent was removed in vacuo The residue was subjected to Kugelrohr distillation

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ozone was introduced into a mixture of 225.5 mg (1 mmol) of (+)-2,2-dimethyl-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-one (96% ee) obtained in Example 4 and 20 ml of methanol at -78° C. for 5 hours, and 2 ml of dimethyl sulfide were added thereto, followed by stirring at the same temperature for 2 hours. The temperature was gradually returned to room temperature, and the solution was then stirred for 5 hours. Afterward, the solvent was distilled off, and the resultant residue was then dissolved in ethanol. 3 drops of concentrated sulfuric acid were added thereto, and the solution was then heated at 80° C. for 30 minutes. Next, ethanol was distilled off, and the residue was diluted with water. The solution was extracted with dichloromethane and then dried over anhydrous sodium sulfate, and the solvent was distilled off and the residue was then subjected to column chromatography (an eluent of hexane:ethyl acetate=5:1), thereby obtaining 109.4 mg (yield 66%) of (+)-ethyl 4-chloro-3-hydroxybutanoate. was gradually returned to room temperature the solution was then stirred for 5 hours Afterward, the solvent was distilled off the resultant residue was then dissolved in ethanol 3 drops of concentrated sulfuric acid were added Next, ethanol was distilled off the residue was diluted with water The solution was extracted with dichloromethane dried over anhydrous sodium sulfate the solvent was distilled off

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

Procedure: The resulting product was esterified with (R)α-methoxy-α-trifluoromethylphenylacetyl chloride, and the ester was analyzed by HPLC. From the area ratio of the chromatogram, the optical yield of the product was found to be 97.2% ee.

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

Procedure: The resulting product was esterified with (R)α-methoxy-α-trifluoromethylphenylacetyl chloride, and the ester was analyzed by HPLC. From the area ratio of the chromatogram, the optical yield of the product was found to be 97.2% ee.