(1R,2R)-2-fluorocyclohexan-1-ol

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

Procedure: 26 mg of trans-2-fluoro-cyclohexanol were added under argon atmosphere at 0° C. to a suspension of 10 mg of sodium hydride (60% in mineral oil) in 2 ml of N,N-dimethylformamide. After 15 min a solution of 100 mg of [4-(5-methanesulfonyl-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester in 1 ml of N,N-dimethylformamide was slowly added. After 12 h at room temperature the mixture was quenched by the addition of water and extracted twice with ethyl acetate. The combined organic layers were dried and concentrated in vacuo. 101 mg of the title compound were obtained. After 12 h at room temperature the mixture was quenched by the addition of water extracted twice with ethyl acetate The combined organic layers were dried concentrated in vacuo

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

Procedure: 26 mg of trans-2-fluoro-cyclohexanol were added under argon atmosphere at 0° C. to a suspension of 10 mg of sodium hydride (60% in mineral oil) in 2 ml of N,N-dimethylformamide. After 15 min a solution of 100 mg of [4-(5-methanesulfonyl-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester in 1 ml of N,N-dimethylformamide was slowly added. After 12 h at room temperature the mixture was quenched by the addition of water and extracted twice with ethyl acetate. The combined organic layers were dried and concentrated in vacuo. 101 mg of the title compound were obtained. After 12 h at room temperature the mixture was quenched by the addition of water extracted twice with ethyl acetate The combined organic layers were dried concentrated in vacuo

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

Procedure: 1-Chloropropyl chloroformate [CAS No. 92600-20-9] (2.99 g) and pyridine (1.62 mL) were dissolved in dichloromethane (30 mL), and a solution of trans-2-fluorocyclohexanol [CAS No. 14365-32-3] (2.36 g) in dichloromethane was added dropwise thereto under ice-cooling. After stirring the resulting mixture overnight at room temperature, the reaction mixture was diluted with ethyl acetate, and sequentially washed with 1 N hydrochloric acid, water, and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate. The resulting mixture was filtered, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate) to obtain the captioned compound (2.731 g). under ice-cooling sequentially washed with 1 N hydrochloric acid, water, and saturated aqueous sodium chloride solution The organic layer was dried over anhydrous magnesium sulfate The resulting mixture was filtered the filtrate obtained was concentrated under reduced pressure The residue obtained was purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate)

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

Procedure: Under an atmosphere of argon and at 0 C, 26 mg of trans-2-fluorocyclohexanol were added to a suspension of 10 mg of sodium hydride (60% in mineral oil) in 2 ml of N,N-dimethylformamide. After 15 min, a solution of 100 mg of tert-butyl [4-(5-methanesulfonyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate in 1 ml of N,N-dimethylformamide was slowly added. After 12 h at room temperature, the mixture was quenched by addition of water and extracted twice with ethyl acetate. The combined organic layers were dried and concentrated under reduced pressure. This gave 101 mg of the title compound. After 12 h at room temperature the mixture was quenched by addition of water extracted twice with ethyl acetate The combined organic layers were dried concentrated under reduced pressure

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

Procedure: 26 mg of trans-2-fluoro-cyclohexanol were added under argon atmosphere at 0° C. to a suspension of 10 mg of sodium hydride (60% in mineral oil) in 2 ml of N,N-dimethylformamide. After 15 min a solution of 100 mg of [4-(5-methanesulfonyl-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester in 1 ml of N,N-dimethylformamide was slowly added. After 12 h at room temperature the mixture was quenched by the addition of water and extracted twice with ethyl acetate. The combined organic layers were dried and concentrated in vacuo. 101 mg of the title compound were obtained. After 12 h at room temperature the mixture was quenched by the addition of water extracted twice with ethyl acetate The combined organic layers were dried concentrated in vacuo