(4-pentylcyclohexyl)methanol

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: 8.0 g of 4-n-pentylcyclohexylmethanol was dissolved in a mixture solvent of 8 ml of pyridine and 8 ml of toluene. To the solution, 6.0 g of methanesulfonyl chloride was added dropwise below 10° C., followed by stirring overnight at room temperature. After the reaction, the reaction mixture was poured into cold water and subjected to extraction with toluene, followed by washing successively with 5%-hydrochloric acid aqueous solution and water and drying with anhydrous magnesium sulfate. The resultant organic layer was subjected to filtration, followed by distilling-off of the solvent to obtain 11.3 g of 4-n-pentylcyclohexylmethyl methanesulfonate. After the reaction subjected to extraction with toluene by washing successively with 5%-hydrochloric acid aqueous solution and water drying with anhydrous magnesium sulfate The resultant organic layer was subjected to filtration

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

Procedure: To a dispersion of 1.75 g of aluminum lithium hydride in 40 ml of dry ether, a solution of 10 g of 4-n-pentylcyclohexanecarbonyl chloride in 12 ml of ether was added dropwise below 5° C., followed by stirring overnight at room temperature. After the reaction, the reaction mixture was acidified with 5%-hydrochloric acid aqueous solution until a pH value of 1 were shown and was subjected to extraction with ether. The organic layer was washed successively with water, 5%-sodium hydroxide, and water, followed by drying with anhydrous magnesium sulfate. The resultant organic layer was subjected to filtration, followed by distilling-off of the solvent to obtain 8.2 g of 4-n-pentylcyclohexylmethanol. After the reaction was subjected to extraction with ether The organic layer was washed successively with water, 5%-sodium hydroxide, and water by drying with anhydrous magnesium sulfate The resultant organic layer was subjected to filtration

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

Procedure: To a solution of 4-{2-[2-(4-benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]ethyl}phenol (970 mg, 2.53 mmol), 4-pentylcyclohexylmethanol (699 mg, 3.79 mmol) and triphenylphosphine (994 mg, 3.79 mmol) in toluene (2 ml) was added 1,1′-(azodicarbonyl)dipiperidine (956 mg, 3.79 mmol) and the mixture was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate anhydride and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as a solid. 1.11 g (yield: 79.9%) the mixture was extracted with ethyl acetate The extract was dried over magnesium sulfate anhydride the solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)

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

Procedure: To a solution of 4-{2-[2-(4-benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]ethyl}phenol (970 mg, 2.53 mmol), 4-pentylcyclohexylmethanol (699 mg, 3.79 mmol) and triphenylphosphine (994 mg, 3.79 mmol) in toluene (2 ml) was added 1,1′-(azodicarbonyl)dipiperidine (956 mg, 3.79 mmol) and the mixture was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate anhydride and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as a solid. 1.11 g (yield: 79.9%) the mixture was extracted with ethyl acetate The extract was dried over magnesium sulfate anhydride the solvent was removed under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)

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

Procedure: 8.0 g of 4-n-pentylcyclohexylmethanol was dissolved in a mixture solvent of 8 ml of pyridine and 8 ml of toluene. To the solution, 6.0 g of methanesulfonyl chloride was added dropwise below 10° C., followed by stirring overnight at room temperature. After the reaction, the reaction mixture was poured into cold water and subjected to extraction with toluene, followed by washing successively with 5%-hydrochloric acid aqueous solution and water and drying with anhydrous magnesium sulfate. The resultant organic layer was subjected to filtration, followed by distilling-off of the solvent to obtain 11.3 g of 4-n-pentylcyclohexylmethyl methanesulfonate. After the reaction subjected to extraction with toluene by washing successively with 5%-hydrochloric acid aqueous solution and water drying with anhydrous magnesium sulfate The resultant organic layer was subjected to filtration

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

Procedure: To a dispersion of 1.75 g of aluminum lithium hydride in 40 ml of dry ether, a solution of 10 g of 4-n-pentylcyclohexanecarbonyl chloride in 12 ml of ether was added dropwise below 5° C., followed by stirring overnight at room temperature. After the reaction, the reaction mixture was acidified with 5%-hydrochloric acid aqueous solution until a pH value of 1 were shown and was subjected to extraction with ether. The organic layer was washed successively with water, 5%-sodium hydroxide, and water, followed by drying with anhydrous magnesium sulfate. The resultant organic layer was subjected to filtration, followed by distilling-off of the solvent to obtain 8.2 g of 4-n-pentylcyclohexylmethanol. After the reaction was subjected to extraction with ether The organic layer was washed successively with water, 5%-sodium hydroxide, and water by drying with anhydrous magnesium sulfate The resultant organic layer was subjected to filtration

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

Procedure: To a slurry of (4-pentyl-cyclohexyl)-methanol (21) (1 equi.), benzyltriethylammonium chloride (0.05 equi.), potassium carbonate (0.15 equi.), and sodium periodate (1.5 equi.) in chloroform-water (1:1) (2 mL/mmole), ruthenium chloride (0.03 equi.) was added at room temperature. The reaction mixture was stirred at 60 C for 2 h. 2-Propanol (0.3 equi.) was added and the reaction mixture was stirred for another 30 min at 60 C, cooled to room temperature, filtered through celite, extracted with dichloromethane, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (dichloromethane) afforded 4-pentyl-cyclohexanecarboxaldehyde (22) as a colorless oil (83%). the reaction mixture was stirred for another 30 min at 60 C filtered through celite extracted with dichloromethane dried over MgSO4 concentrated in vacuo Purification by chromatography on silica gel (dichloromethane)

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

Procedure: To a slurry of lithium aluminum hydride (2 equi.) in diethyl ether (4 mL/mmole), a solution of commercially available 4-pentylcyclohexanecarboxylic acid (20) (1 equi.) in diethyl ether (3 ml/mmole) was added at ice temperature over a period of 20 min. The reaction mixture was stirred at room temperature for 24 h, cooled to ice temperature, quenched slowly with water (1 mL/g LAH), 15% aqueous sodium hydroxide (1 mL/g LAH), and water (3 mL/g LAH) consecutively. MgSO4 (5 g/100 mL reaction solution) was added to the reaction mixture, stirred for 30 min, filtered through celite, and concentrated in vacuo to give (4-pentyl-cyclohexyl)-methanol (21) a colorless oil (95%). cooled to ice temperature quenched slowly with water (1 mL/g LAH), 15% aqueous sodium hydroxide (1 mL/g LAH), and water (3 mL/g LAH) consecutively MgSO4 (5 g/100 mL reaction solution) was added to the reaction mixture stirred for 30 min filtered through celite concentrated in vacuo

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

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

Procedure: To a slurry of (4-pentyl-cyclohexyl)-methanol (21) (1 equi.), benzyltriethylammonium chloride (0.05 equi.), potassium carbonate (0.15 equi.), and sodium periodate (1.5 equi.) in chloroform-water (1:1) (2 mL/mmole), ruthenium chloride (0.03 equi.) was added at room temperature. The reaction mixture was stirred at 60 C for 2 h. 2-Propanol (0.3 equi.) was added and the reaction mixture was stirred for another 30 min at 60 C, cooled to room temperature, filtered through celite, extracted with dichloromethane, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (dichloromethane) afforded 4-pentyl-cyclohexanecarboxaldehyde (22) as a colorless oil (83%). the reaction mixture was stirred for another 30 min at 60 C filtered through celite extracted with dichloromethane dried over MgSO4 concentrated in vacuo Purification by chromatography on silica gel (dichloromethane)