(4-tert-butylcyclohexyl)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: To a cooled (0° C.) solution of 4-tert-butylcyclohexane-carboxylic acid (3.00 g, 16.3 mmoles) in THF (30 mL) is slowly added a THF solution of borane-THF complex (1.0M, 21.2 mL, 21.2 mmoles). The solution is stirred at room temperature for 18 hours, then quenched with 2N HCl solution (30 mL), and extracted with EtOAc. The organic layer is isolated, washed with 1N NaOH, dried over sodium sulfate, and concentrated to yield the title compound as a clear oil. 1H NMR (300 MHz, CDCl3): δ 2.06 (d, 2H), 1.82 (m, 4H), 1.52 (m, 2H), 0.88 (m, 4H), 0.83 (s, 9H). quenched with 2N HCl solution (30 mL) extracted with EtOAc The organic layer is isolated washed with 1N NaOH dried over sodium sulfate concentrated

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

Procedure: To a solution of 4-(1,1-dimethylethyl)cyclohexanemethanol (1.0 g, 5.9 mmol) in CH2Cl2 (distilled from CaH2) (43 mL) were added at room temperature under argon anhydrous NaOAc (3.84 g, 46.8 mmol). After stirring at room temperature for 5 minutes pyridinium chlorochromate (3.84 g, 17.8 mmol) was added and after stirring for 1 h at room temperature, the reaction was quenched by addition of ethyl ether (200 mL). The crude reaction was filtered through a Fluorasil column to give crude 4-(1,1-dimethylethyl)cyclohexanecarboxaldehyde (0.862 g, 5.12 mmol) as a mixture of trans and cis isomer in 87% yield. was added the reaction was quenched by addition of ethyl ether (200 mL) The crude reaction was filtered through a Fluorasil column

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

Procedure: To a solution of 4-tert-butylcyclohexane carboxylic acid (10.0 g, 54.3 mmol of a mixture of cis and trans isomers) in anhydrous THF (distilled over Na/benzophenone) (44 mL) at 0° C., under argon were added dropwise B2H6 in THF (66.5 mL of 0.98M, 65.2 mmol). The reaction mixture was stirred at 0° C. for 2 hrs and then placed in the freezer overnight. The reaction was quenched by addition of saturated NaCl solution (50 mL) and was concentrated. The aqueous residue was extracted with EtOAc (3×200 mL) and the combined organic extracts were washed with sat. NaHCO3 solution (250 mL), followed by saturated brine (250 mL), dried over Na2SO4, and filtered. Concentration to dryness yielded 9.96 g of crude product which was purified via flash chromatography eluting with 25% EtOAc in hexane to yield an amorphous 4-(1,1-dimethylethyl)cyclohexanemethanol (9.18 g, 53.9 mmol) as a mixture of cis and trans isomers in 99% yield. placed in the freezer overnight The reaction was quenched by addition of saturated NaCl solution (50 mL) was concentrated The aqueous residue was extracted with EtOAc (3×200 mL) the combined organic extracts were washed with sat. NaHCO3 solution (250 mL) dried over Na2SO4 filtered Concentration to dryness yielded 9.96 g of crude product which was purified via flash chromatography eluting with 25% EtOAc in hexane

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

Procedure: To a solution of 4-tert-butylcyclohexane carboxylic acid (10.0 g, 54.3 mmol of a mixture of cis and trans isomers) in anhydrous THF (distilled over Na/benzophenone) (44 mL) at 0° C., under argon were added dropwise B2H6 in THF (66.5 mL of 0.98M, 65.2 mmol). The reaction mixture was stirred at 0° C. for 2 hrs and then placed in the freezer overnight. The reaction was quenched by addition of saturated NaCl solution (50 mL) and was concentrated. The aqueous residue was extracted with EtOAc (3×200 mL) and the combined organic extracts were washed with sat. NaHCO3 solution (250 mL), followed by saturated brine (250 mL), dried over Na2SO4, and filtered. Concentration to dryness yielded 9.96 g of crude product which was purified via flash chromatography eluting with 25% EtOAc in hexane to yield an amorphous 4-(1,1-dimethylethyl)cyclohexanemethanol (9.18 g, 53.9 mmol) as a mixture of cis and trans isomers in 99% yield. placed in the freezer overnight The reaction was quenched by addition of saturated NaCl solution (50 mL) was concentrated The aqueous residue was extracted with EtOAc (3×200 mL) the combined organic extracts were washed with sat. NaHCO3 solution (250 mL) dried over Na2SO4 filtered Concentration to dryness yielded 9.96 g of crude product which was purified via flash chromatography eluting with 25% EtOAc in hexane

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: To a cooled (0° C.) solution of 4-tert-butylcyclohexane-carboxylic acid (3.00 g, 16.3 mmoles) in THF (30 mL) is slowly added a THF solution of borane-THF complex (1.0M, 21.2 mL, 21.2 mmoles). The solution is stirred at room temperature for 18 hours, then quenched with 2N HCl solution (30 mL), and extracted with EtOAc. The organic layer is isolated, washed with 1N NaOH, dried over sodium sulfate, and concentrated to yield the title compound as a clear oil. 1H NMR (300 MHz, CDCl3): δ 2.06 (d, 2H), 1.82 (m, 4H), 1.52 (m, 2H), 0.88 (m, 4H), 0.83 (s, 9H). quenched with 2N HCl solution (30 mL) extracted with EtOAc The organic layer is isolated washed with 1N NaOH dried over sodium sulfate concentrated

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

Procedure: To a solution of 4-(1,1-dimethylethyl)cyclohexanemethanol (1.0 g, 5.9 mmol) in CH2Cl2 (distilled from CaH2) (43 mL) were added at room temperature under argon anhydrous NaOAc (3.84 g, 46.8 mmol). After stirring at room temperature for 5 minutes pyridinium chlorochromate (3.84 g, 17.8 mmol) was added and after stirring for 1 h at room temperature, the reaction was quenched by addition of ethyl ether (200 mL). The crude reaction was filtered through a Fluorasil column to give crude 4-(1,1-dimethylethyl)cyclohexanecarboxaldehyde (0.862 g, 5.12 mmol) as a mixture of trans and cis isomer in 87% yield. was added the reaction was quenched by addition of ethyl ether (200 mL) The crude reaction was filtered through a Fluorasil column

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

Procedure: To a solution of 4-tert-butylcyclohexane carboxylic acid (10.0 g, 54.3 mmol of a mixture of cis and trans isomers) in anhydrous THF (distilled over Na/benzophenone) (44 mL) at 0° C., under argon were added dropwise B2H6 in THF (66.5 mL of 0.98M, 65.2 mmol). The reaction mixture was stirred at 0° C. for 2 hrs and then placed in the freezer overnight. The reaction was quenched by addition of saturated NaCl solution (50 mL) and was concentrated. The aqueous residue was extracted with EtOAc (3×200 mL) and the combined organic extracts were washed with sat. NaHCO3 solution (250 mL), followed by saturated brine (250 mL), dried over Na2SO4, and filtered. Concentration to dryness yielded 9.96 g of crude product which was purified via flash chromatography eluting with 25% EtOAc in hexane to yield an amorphous 4-(1,1-dimethylethyl)cyclohexanemethanol (9.18 g, 53.9 mmol) as a mixture of cis and trans isomers in 99% yield. placed in the freezer overnight The reaction was quenched by addition of saturated NaCl solution (50 mL) was concentrated The aqueous residue was extracted with EtOAc (3×200 mL) the combined organic extracts were washed with sat. NaHCO3 solution (250 mL) dried over Na2SO4 filtered Concentration to dryness yielded 9.96 g of crude product which was purified via flash chromatography eluting with 25% EtOAc in hexane