propan-2-yl 4,4,4-trifluoro-3-oxobutanoate

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

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

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isopropyl 4,4,4-trifluoroacetoacetate (50 g), under a blanket of nitrogen gas, is heated to 40° C. and treated with platinum (0.1 g of 5% Pt/C, 0.01% load) and triethylamine (0.2 g, 0.4 % load). Hydrogen is charged to a pressure of 5 bars, and the mixture agitated at 40° C. for 6h. After filtration to remove the catalyst, 48.5 g (96% yield) of isopropyl 4,4,4-trifluoro-3-hydroxybutyrate is obtained. After filtration to remove the catalyst

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

Procedure: 100 mg (0.53 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 105 mg (0.53 mmol) of isopropyl 4,4,4-trifluoro-3-oxobutanoate, 43.6 mg (0.53 mmol) of 3-aminocrotononitrile and 46 μl (0.79 mmol) of acetic acid in 5 ml of 2-propanol and heated under reflux under argon for 4 h. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. The main product obtained in this way is stirred under reflux in acetic acid overnight. The solution is concentrated and the residue is recrystallized from diethyl ether. 75 mg (33% of theory) of the title compound are obtained as a white solid. heated under reflux under argon for 4 h The solvent is removed in vacuo the residue is purified by preparative HPLC The main product obtained in this way The solution is concentrated the residue is recrystallized from diethyl ether

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isopropyl 4,4,4-trifluoroacetoacetate (50 g), under a blanket of nitrogen gas, is heated to 40° C. and treated with platinum (0.1 g of 5% Pt/C, 0.01% load) and triethylamine (0.2 g, 0.4 % load). Hydrogen is charged to a pressure of 5 bars, and the mixture agitated at 40° C. for 6h. After filtration to remove the catalyst, 48.5 g (96% yield) of isopropyl 4,4,4-trifluoro-3-hydroxybutyrate is obtained. After filtration to remove the catalyst

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isopropyl 4,4,4-trifluoroacetoacetate (50 g), under a blanket of nitrogen gas, is heated to 40° C. and treated with platinum (0.1 g of 5% Pt/C, 0.01% load) and triethylamine (0.2 g, 0.4 % load). Hydrogen is charged to a pressure of 5 bars, and the mixture agitated at 40° C. for 6h. After filtration to remove the catalyst, 48.5 g (96% yield) of isopropyl 4,4,4-trifluoro-3-hydroxybutyrate is obtained. After filtration to remove the catalyst

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: 100 mg (0.53 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 105 mg (0.53 mmol) of isopropyl 4,4,4-trifluoro-3-oxobutanoate, 43.6 mg (0.53 mmol) of 3-aminocrotononitrile and 46 μl (0.79 mmol) of acetic acid in 5 ml of 2-propanol and heated under reflux under argon for 4 h. The solvent is removed in vacuo, and the residue is purified by preparative HPLC. The main product obtained in this way is stirred under reflux in acetic acid overnight. The solution is concentrated and the residue is recrystallized from diethyl ether. 75 mg (33% of theory) of the title compound are obtained as a white solid. heated under reflux under argon for 4 h The solvent is removed in vacuo the residue is purified by preparative HPLC The main product obtained in this way The solution is concentrated the residue is recrystallized from diethyl ether

Conditions: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 6 mL of tetrahydrofuran were dissolved 6.4 mg of RuCl[(1R,2R)-p-TsNHCH(C6H5)CH(C6H5)NH2] (p-cymene), 5 mL of a mixture of formic acid-triethylamine (5:2 in molar ratio), 1.0 g of isopropyl 4,4,4-trifluoro-3-oxobutanoate, and the whole was stirred at 35° C. for 15 hours, followed by concentration under reduced pressure using an evaporator. To the resulting concentrate were added 10 mL of water and 10 mL of ethyl acetate, and then a saturated sodium carbonate aqueous solution was added thereto under stirring until the pH became 7 or higher. The ethyl acetate layer separated from the aqueous layer was concentrated to obtain optically active isopropyl 4,4,4-trifluoro-3-hydroxybutanoate. Upon the measurement under the above conditions, the optical purity and conversion were found to be 96.2% e.e. and 100%, respectively. followed by concentration under reduced pressure an evaporator To the resulting concentrate were added 10 mL of water and 10 mL of ethyl acetate a saturated sodium carbonate aqueous solution was added under stirring until the pH The ethyl acetate layer separated from the aqueous layer was concentrated

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

Procedure: The preparation was carried out analogously to preparation example 1 using isopropyl 4,4,4-trifluoro-3-oxobutyrate and triisopropyl orthoformate.

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isopropyl 4,4,4-trifluoroacetoacetate (50 g), under a blanket of nitrogen gas, is heated to 40° C. and treated with platinum (0.1 g of 5% Pt/C, 0.01% load) and triethylamine (0.2 g, 0.4 % load). Hydrogen is charged to a pressure of 5 bars, and the mixture agitated at 40° C. for 6h. After filtration to remove the catalyst, 48.5 g (96% yield) of isopropyl 4,4,4-trifluoro-3-hydroxybutyrate is obtained. After filtration to remove the catalyst