2-cyclohexyl-2-methylpropan-1-ol

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Oxalyl chloride (7.8 g, 61.42 mmol) in methylene chloride (60 mL) at −78° C. was treated with dimethylsufoxide (8.4 g, 107.5 mmol). After stirring at −78° C. for 10 minutes, the mixture was treated with 2-cyclohexyl-2-methylpropanol (4.8 g, 36.86 mmol) in 15 ml of methylene chloride. The mixture was allowed to stir at −78° C. for 30 minutes and then treated with triethylamine (15.54 g, 153.6 mmol). The reaction mixture was stirred for 10 minutes and then stirred an additional 5 minutes at 0° C. The mixture was quenched with saturated aqueous ammonium (10 mL) chloride and extracted with diethyl ether (2×50 mL). The organic layer was washed with brine (15 mL), dried over anhydrous sodium sulfate and concentrated under vacuo. The crude product was redissolved in diethyl ether and the resulting precipitate was filtered through a pad of Celite. The solution was concentrated under reduced pressure to provide 4.5 g of 2-cyclohexyl-2-methylpropanal as an oil. to stir at −78° C. for 30 minutes The reaction mixture was stirred for 10 minutes stirred an additional 5 minutes at 0° C The mixture was quenched with saturated aqueous ammonium (10 mL) chloride extracted with diethyl ether (2×50 mL) The organic layer was washed with brine (15 mL) dried over anhydrous sodium sulfate concentrated under vacuo The crude product was redissolved in diethyl ether the resulting precipitate was filtered through a pad of Celite The solution was concentrated under reduced pressure

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

Procedure: 2-Cyclohexyl-2-methyl-1-propanol, oxalyl chloride and dimethylsulfoxide were processed as described in Example 18A to provide the title compound.

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

Procedure: The title compound was prepared from 5-{2-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-propyl}-benzo-[1,3]dioxole-2,2-dicarboxylic acid and 2-cyclohexyl-2-methylpropanol according to the procedure of Example 1 as an off-white solid; 1H NMR (DMSO-d6,400 MHz) δ 1.1 (s, 6H, CH3, CH3), 1.45 (s, 6H, CH3, CH3), 1.5 (s, 6H, CH3, CH3), 2.6 (m, 1H, CH), 3-3.3 (m, 3H, CH, CH2), 3.4 (brs, 1H, CH), 4.04 (s, 4H, OCH2, OCH2), 5.05 (m, 1H, CH), 6.35 (d, J=4.17 Hz, 1H, OH), 6.85 (dd, J=7.9, 1.32 Hz, 1H, Ar--H), 7.07 (m, 2H, Ar--H), 7.38-7.42 (m, 3H, Ar--H), 7.5 (s, 1H, Ar--H), 8.8 (brs, 1H, NH), 9.4 (brs, 1H, NH); IR (KBr, cm-1) 3400 (OH), 2900 (NH), 1760 (CO); MS m/e 698 (M+H)+ ; Analysis for: C40H56ClNO7 ×HCl: Calc'd: C, 65.38; H, 7.82; N, 1.91; Found: C, 65.32; H, 7.96; N, 1.94.

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Oxalyl chloride (7.8 g, 61.42 mmol) in methylene chloride (60 mL) at −78° C. was treated with dimethylsufoxide (8.4 g, 107.5 mmol). After stirring at −78° C. for 10 minutes, the mixture was treated with 2-cyclohexyl-2-methylpropanol (4.8 g, 36.86 mmol) in 15 ml of methylene chloride. The mixture was allowed to stir at −78° C. for 30 minutes and then treated with triethylamine (15.54 g, 153.6 mmol). The reaction mixture was stirred for 10 minutes and then stirred an additional 5 minutes at 0° C. The mixture was quenched with saturated aqueous ammonium (10 mL) chloride and extracted with diethyl ether (2×50 mL). The organic layer was washed with brine (15 mL), dried over anhydrous sodium sulfate and concentrated under vacuo. The crude product was redissolved in diethyl ether and the resulting precipitate was filtered through a pad of Celite. The solution was concentrated under reduced pressure to provide 4.5 g of 2-cyclohexyl-2-methylpropanal as an oil. to stir at −78° C. for 30 minutes The reaction mixture was stirred for 10 minutes stirred an additional 5 minutes at 0° C The mixture was quenched with saturated aqueous ammonium (10 mL) chloride extracted with diethyl ether (2×50 mL) The organic layer was washed with brine (15 mL) dried over anhydrous sodium sulfate concentrated under vacuo The crude product was redissolved in diethyl ether the resulting precipitate was filtered through a pad of Celite The solution was concentrated under reduced pressure