methyl 2-(4,4-dimethylcyclohexyl)acetate

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

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

Procedure: Hydrolysis of (4,4-dimethyl-cyclohexyl)-acetic acid methyl ester (80 mg, 0.43 mmol) with NaOH following a method analogous to General Procedure G1 gave (4,4-dimethyl-cyclohexyl)-acetic acid after purification (70 mg, 95% yield). This acid (70 mg) was converted to 1-(4,4-dimethyl-cyclohexyl)-propan-2-one (60.0 mg, 89% yield) using MeLi in ethyl ether following a method analogous to General Procedure A1. Pyrrolidone hydrotribromide (190 mg, 0.38 mmol) treatment of the above ketone following a method analogous to General Procedure B1 gave 1-bromo-3-(4,4-dimethyl-cyclohexyl)-propan-2-one (70 mg).

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

Procedure: Hydrolysis of (4,4-dimethyl-cyclohexyl)-acetic acid methyl ester (80 mg, 0.43 mmol) with NaOH following a method analogous to General Procedure G1 gave (4,4-dimethyl-cyclohexyl)-acetic acid after purification (70 mg, 95% yield). This acid (70 mg) was converted to 1-(4,4-dimethyl-cyclohexyl)-propan-2-one (60.0 mg, 89% yield) using MeLi in ethyl ether following a method analogous to General Procedure A1. Pyrrolidone hydrotribromide (190 mg, 0.38 mmol) treatment of the above ketone following a method analogous to General Procedure B1 gave 1-bromo-3-(4,4-dimethyl-cyclohexyl)-propan-2-one (70 mg).

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

Procedure: To a stirred solution of the above alkene (100 mg, 0.54 mmol) in a mixture of ethyl acetate-methanol (0.8 mL, 1:1) was added Pd—C (10 mg, 20% on activated carbon) and the resultant mixture was stirred under hydrogen pressure (50 psi) for 2 h in a resealable glass pressure vessel equipped with a manometer and pressure valve. The catalyst was filtered off using a pad of Celite® and the Celite® pad was washed with an ethyl acetate-methanol mixture (1:1, about 10 mL). The combined filtrate was concentrated under reduced pressure to give the desired (4,4-dimethyl-cyclohexyl)-acetic acid methyl ester (80 mg). equipped with a manometer and pressure valve The catalyst was filtered off the Celite® pad was washed with an ethyl acetate-methanol mixture (1:1, about 10 mL) The combined filtrate was concentrated under reduced pressure

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

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

Procedure: Hydrolysis of (4,4-dimethyl-cyclohexyl)-acetic acid methyl ester (80 mg, 0.43 mmol) with NaOH following a method analogous to General Procedure G1 gave (4,4-dimethyl-cyclohexyl)-acetic acid after purification (70 mg, 95% yield). This acid (70 mg) was converted to 1-(4,4-dimethyl-cyclohexyl)-propan-2-one (60.0 mg, 89% yield) using MeLi in ethyl ether following a method analogous to General Procedure A1. Pyrrolidone hydrotribromide (190 mg, 0.38 mmol) treatment of the above ketone following a method analogous to General Procedure B1 gave 1-bromo-3-(4,4-dimethyl-cyclohexyl)-propan-2-one (70 mg).

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

Procedure: To a stirred solution of the above alkene (100 mg, 0.54 mmol) in a mixture of ethyl acetate-methanol (0.8 mL, 1:1) was added Pd—C (10 mg, 20% on activated carbon) and the resultant mixture was stirred under hydrogen pressure (50 psi) for 2 h in a resealable glass pressure vessel equipped with a manometer and pressure valve. The catalyst was filtered off using a pad of Celite® and the Celite® pad was washed with an ethyl acetate-methanol mixture (1:1, about 10 mL). The combined filtrate was concentrated under reduced pressure to give the desired (4,4-dimethyl-cyclohexyl)-acetic acid methyl ester (80 mg). equipped with a manometer and pressure valve The catalyst was filtered off the Celite® pad was washed with an ethyl acetate-methanol mixture (1:1, about 10 mL) The combined filtrate was concentrated under reduced pressure