(4-methoxycyclohexyl)methanol

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

Procedure: To a mixture of (4-methoxy-cyclohexyl)-methanol (1.25 g, 8.7 mmol) and trifluoromethanesulfonic acid 3-bromo-propyl ester (2.58 g, 9.55 mmol) in nitromethane (15 ml) was added 2,6-di-tert-butylpyridine (1.83 ml, 9.55 mmol). The reaction mixture was heated at 80° C. for 18 hours. The mixture was concentrated in vacuo and the residue purified by flash column chromatography on silica eluting with 20% ethyl acetate in hexane to give the title compound as a yellow oil (1.4 g, 61%). The mixture was concentrated in vacuo the residue purified by flash column chromatography on silica eluting with 20% ethyl acetate in hexane

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

Procedure: 4-Methoxycyclohexanecarboxylic acid (7 g) in tetrahydrofuran (20 mL) was treated with 1 M (in tetrahydrofuran) borane-tetrahydrofuran complex (100 mL) overnight. The mixture was concentrated and the residue was dissolved in methanol (100 mL) and concentrated HCl (10 mL). The resulting mixture was stirred for 1 hour and concentrated. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound. The mixture was concentrated the residue was dissolved in methanol (100 mL) concentrated The residue was dissolved in dichloromethane washed with water The organic layer was dried over Na2SO4 filtered concentrated

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

Procedure: 4-Methoxycyclohexanecarboxylic acid (7 g) in tetrahydrofuran (20 mL) was treated with 1 M (in tetrahydrofuran) borane-tetrahydrofuran complex (100 mL) overnight. The mixture was concentrated and the residue was dissolved in methanol (100 mL) and concentrated HCl (10 mL). The resulting mixture was stirred for 1 hour and concentrated. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound. The mixture was concentrated the residue was dissolved in methanol (100 mL) concentrated The residue was dissolved in dichloromethane washed with water The organic layer was dried over Na2SO4 filtered concentrated

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

Procedure: 4-Methoxycyclohexanecarboxylic acid (7 g) in tetrahydrofuran (20 mL) was treated with 1 M (in tetrahydrofuran) borane-tetrahydrofuran complex (100 mL) overnight. The mixture was concentrated and the residue was dissolved in methanol (100 mL) and concentrated HCl (10 mL). The resulting mixture was stirred for 1 hour and concentrated. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound. The mixture was concentrated the residue was dissolved in methanol (100 mL) concentrated The residue was dissolved in dichloromethane washed with water The organic layer was dried over Na2SO4 filtered concentrated

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

Procedure: 4-Methoxycyclohexanecarboxylic acid (7 g) in tetrahydrofuran (20 mL) was treated with 1 M (in tetrahydrofuran) borane-tetrahydrofuran complex (100 mL) overnight. The mixture was concentrated and the residue was dissolved in methanol (100 mL) and concentrated HCl (10 mL). The resulting mixture was stirred for 1 hour and concentrated. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound. The mixture was concentrated the residue was dissolved in methanol (100 mL) concentrated The residue was dissolved in dichloromethane washed with water The organic layer was dried over Na2SO4 filtered concentrated

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

Procedure: 4-Methoxycyclohexanecarboxylic acid (7 g) in tetrahydrofuran (20 mL) was treated with 1 M (in tetrahydrofuran) borane-tetrahydrofuran complex (100 mL) overnight. The mixture was concentrated and the residue was dissolved in methanol (100 mL) and concentrated HCl (10 mL). The resulting mixture was stirred for 1 hour and concentrated. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound. The mixture was concentrated the residue was dissolved in methanol (100 mL) concentrated The residue was dissolved in dichloromethane washed with water The organic layer was dried over Na2SO4 filtered concentrated

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

Procedure: 4-Methoxycyclohexanecarboxylic acid (7 g) in tetrahydrofuran (20 mL) was treated with 1 M (in tetrahydrofuran) borane-tetrahydrofuran complex (100 mL) overnight. The mixture was concentrated and the residue was dissolved in methanol (100 mL) and concentrated HCl (10 mL). The resulting mixture was stirred for 1 hour and concentrated. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound. The mixture was concentrated the residue was dissolved in methanol (100 mL) concentrated The residue was dissolved in dichloromethane washed with water The organic layer was dried over Na2SO4 filtered concentrated

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

Procedure: To a mixture of (4-methoxy-cyclohexyl)-methanol (1.25 g, 8.7 mmol) and trifluoromethanesulfonic acid 3-bromo-propyl ester (2.58 g, 9.55 mmol) in nitromethane (15 ml) was added 2,6-di-tert-butylpyridine (1.83 ml, 9.55 mmol). The reaction mixture was heated at 80° C. for 18 hours. The mixture was concentrated in vacuo and the residue purified by flash column chromatography on silica eluting with 20% ethyl acetate in hexane to give the title compound as a yellow oil (1.4 g, 61%). The mixture was concentrated in vacuo the residue purified by flash column chromatography on silica eluting with 20% ethyl acetate in hexane

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

Procedure: 13.7 ml (27.5 mmol) of lithium aluminium hydride solution (2M in THF) was diluted with 82 ml of methyl tert-butyl ether, and a solution of 4.30 g (25.0 mmol) of methyl 4-methoxycyclohexanecarboxylate (cis/trans isomer mixture) in 82 ml of methyl tert-butyl ether was then added dropwise. The reaction solution was stirred at 40° C. for another 6 h and the reaction was then terminated by addition of 10 ml of water and 10 ml of aqueous 10% strength potassium hydroxide solution. The organic phase was decanted, dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. Yield: 3.24 g (90% of theory) the reaction was then terminated by addition of 10 ml of water and 10 ml of aqueous 10% strength potassium hydroxide solution The organic phase was decanted dried over sodium sulphate filtered the solvent was removed under reduced pressure

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

Procedure: 13.7 ml (27.5 mmol) of lithium aluminium hydride solution (2M in THF) was diluted with 82 ml of methyl tert-butyl ether, and a solution of 4.30 g (25.0 mmol) of methyl 4-methoxycyclohexanecarboxylate (cis/trans isomer mixture) in 82 ml of methyl tert-butyl ether was then added dropwise. The reaction solution was stirred at 40° C. for another 6 h and the reaction was then terminated by addition of 10 ml of water and 10 ml of aqueous 10% strength potassium hydroxide solution. The organic phase was decanted, dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. Yield: 3.24 g (90% of theory) the reaction was then terminated by addition of 10 ml of water and 10 ml of aqueous 10% strength potassium hydroxide solution The organic phase was decanted dried over sodium sulphate filtered the solvent was removed under reduced pressure

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

Procedure: 4-Methoxycyclohexanecarboxylic acid (7 g) in tetrahydrofuran (20 mL) was treated with 1 M (in tetrahydrofuran) borane-tetrahydrofuran complex (100 mL) overnight. The mixture was concentrated and the residue was dissolved in methanol (100 mL) and concentrated HCl (10 mL). The resulting mixture was stirred for 1 hour and concentrated. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound. The mixture was concentrated the residue was dissolved in methanol (100 mL) concentrated The residue was dissolved in dichloromethane washed with water The organic layer was dried over Na2SO4 filtered concentrated

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

Procedure: 4-Methoxycyclohexanecarboxylic acid (7 g) in tetrahydrofuran (20 mL) was treated with 1 M (in tetrahydrofuran) borane-tetrahydrofuran complex (100 mL) overnight. The mixture was concentrated and the residue was dissolved in methanol (100 mL) and concentrated HCl (10 mL). The resulting mixture was stirred for 1 hour and concentrated. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound. The mixture was concentrated the residue was dissolved in methanol (100 mL) concentrated The residue was dissolved in dichloromethane washed with water The organic layer was dried over Na2SO4 filtered concentrated