[4-[tert-butyl(dimethyl)silyl]oxycyclohexyl]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:

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

Procedure: Prepared from [4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-methanol and ethyl 3-hydroxybenzoate by a method similar to Example 1.

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: tert-Butyldimethylsilyl chloride (8.8 g, 58 mmol) was added to a solution of ethyl 4-hydroxycyclohexanecarboxylate (10 g, 58 mmol) and imidazole (4.3 g, 64 mmol) in DCM (300 ml), and the mixture was stirred overnight at 20° C. After washing with water (2×100 ml), the organic phase was dried (MgSO4) and evaporated to dryness. The residue was dissolved in dry THF (300 ml) and cooled to −10° C. Dibal-H (1.0 M in toluene, 174 ml, 174 mmol) was added dropwise over a period of 60 min, while the temperature was kept at −10° C. After stirring for 2 hrs the reaction was quenched by slow addition of a saturated ammonium chloride solution (30 ml). The resulting suspension was filtered, and the filtrate was concentrated in vacuo to give 13 g of the title compound as a mixture of two isomers. LC-MS (m/z): 245 (M+1). After washing with water (2×100 ml) the organic phase was dried (MgSO4) evaporated to dryness The residue was dissolved in dry THF (300 ml) cooled to −10° C was kept at −10° C After stirring for 2 hrs the reaction was quenched by slow addition of a saturated ammonium chloride solution (30 ml) The resulting suspension was filtered the filtrate was concentrated in vacuo

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: Prepared from [4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-methanol and ethyl 3-hydroxybenzoate by a method similar to Example 1.

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: tert-Butyldimethylsilyl chloride (8.8 g, 58 mmol) was added to a solution of ethyl 4-hydroxycyclohexanecarboxylate (10 g, 58 mmol) and imidazole (4.3 g, 64 mmol) in DCM (300 ml), and the mixture was stirred overnight at 20° C. After washing with water (2×100 ml), the organic phase was dried (MgSO4) and evaporated to dryness. The residue was dissolved in dry THF (300 ml) and cooled to −10° C. Dibal-H (1.0 M in toluene, 174 ml, 174 mmol) was added dropwise over a period of 60 min, while the temperature was kept at −10° C. After stirring for 2 hrs the reaction was quenched by slow addition of a saturated ammonium chloride solution (30 ml). The resulting suspension was filtered, and the filtrate was concentrated in vacuo to give 13 g of the title compound as a mixture of two isomers. LC-MS (m/z): 245 (M+1). After washing with water (2×100 ml) the organic phase was dried (MgSO4) evaporated to dryness The residue was dissolved in dry THF (300 ml) cooled to −10° C was kept at −10° C After stirring for 2 hrs the reaction was quenched by slow addition of a saturated ammonium chloride solution (30 ml) The resulting suspension was filtered the filtrate was concentrated in vacuo

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: tert-Butyldimethylsilyl chloride (8.8 g, 58 mmol) was added to a solution of ethyl 4-hydroxycyclohexanecarboxylate (10 g, 58 mmol) and imidazole (4.3 g, 64 mmol) in DCM (300 ml), and the mixture was stirred overnight at 20° C. After washing with water (2×100 ml), the organic phase was dried (MgSO4) and evaporated to dryness. The residue was dissolved in dry THF (300 ml) and cooled to −10° C. Dibal-H (1.0 M in toluene, 174 ml, 174 mmol) was added dropwise over a period of 60 min, while the temperature was kept at −10° C. After stirring for 2 hrs the reaction was quenched by slow addition of a saturated ammonium chloride solution (30 ml). The resulting suspension was filtered, and the filtrate was concentrated in vacuo to give 13 g of the title compound as a mixture of two isomers. LC-MS (m/z): 245 (M+1). After washing with water (2×100 ml) the organic phase was dried (MgSO4) evaporated to dryness The residue was dissolved in dry THF (300 ml) cooled to −10° C was kept at −10° C After stirring for 2 hrs the reaction was quenched by slow addition of a saturated ammonium chloride solution (30 ml) The resulting suspension was filtered the filtrate was concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At 0° C., 8.1 g (29.7 mmol) of methyl 4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexanecarboxylate (trans/cis mixture) as a solution in 50 ml of THF were added dropwise to a solution of 50 ml (100 mmol) of lithium aluminium hydride (2M in THF). The mixture was stirred at 0° C. for another 1 h and at RT for another 2 h. 3.8 ml of water, 3.8 ml of aqueous sodium hydroxide solution (15%) and 11.4 ml of water were then added to the reaction in succession, and the precipitate was filtered off. The organic phase was washed with 50 ml of saturated aqueous sodium chloride solution, dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. Yield: 7.00 g (92% of theory) the precipitate was filtered off The organic phase was washed with 50 ml of saturated aqueous sodium chloride solution dried over magnesium sulphate filtered the solvent was removed under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At 0° C., 8.1 g (29.7 mmol) of methyl 4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexanecarboxylate (trans/cis mixture) as a solution in 50 ml of THF were added dropwise to a solution of 50 ml (100 mmol) of lithium aluminium hydride (2M in THF). The mixture was stirred at 0° C. for another 1 h and at RT for another 2 h. 3.8 ml of water, 3.8 ml of aqueous sodium hydroxide solution (15%) and 11.4 ml of water were then added to the reaction in succession, and the precipitate was filtered off. The organic phase was washed with 50 ml of saturated aqueous sodium chloride solution, dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. Yield: 7.00 g (92% of theory) the precipitate was filtered off The organic phase was washed with 50 ml of saturated aqueous sodium chloride solution dried over magnesium sulphate filtered the solvent was removed under reduced pressure