tert-butyl-dimethyl-piperidin-3-yloxysilane

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 3-[(5-bromo-2-methyl-benzoyl)amino]-2,4-dimethyl-benzoate (0.5 g, 1.32 mmol), tert-butyl-dimethyl-(3-piperidyloxy)silane (0.425 g, 1.98 mmol) and Cs2CO3 (1.28 g, 3.96 mmol) in 1,4-dioxane (15 ml) is added Pd2(dba)3 (0.12 g, 0.132 mmol) followed by S-Phos (0.054 g, 0.132 mmol). The reaction mixture is purged with nitrogen for 5 minutes and then heated at 100° C. After 16 hours, the reaction is cooled to ambient temperature, filtered through Celite™, and washed with EtOAc. The combined filtrates are dried over sodium sulfate, filtered, and concentrated under reduced pressure and purified by flash chromatography (silica gel) using 10% EtOAc in hexane to afford the title compound as a brown semi-solid (0.4 g, 60%). The reaction mixture is purged with nitrogen for 5 minutes the reaction is cooled to ambient temperature filtered through Celite™ washed with EtOAc The combined filtrates are dried over sodium sulfate filtered concentrated under reduced pressure purified by flash chromatography (silica gel)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 3-[(5-bromo-2-methyl-benzoyl)amino]-2,4-dimethyl-benzoate (0.5 g, 1.32 mmol), tert-butyl-dimethyl-(3-piperidyloxy)silane (0.425 g, 1.98 mmol) and Cs2CO3 (1.28 g, 3.96 mmol) in 1,4-dioxane (15 ml) is added Pd2(dba)3 (0.12 g, 0.132 mmol) followed by S-Phos (0.054 g, 0.132 mmol). The reaction mixture is purged with nitrogen for 5 minutes and then heated at 100° C. After 16 hours, the reaction is cooled to ambient temperature, filtered through Celite™, and washed with EtOAc. The combined filtrates are dried over sodium sulfate, filtered, and concentrated under reduced pressure and purified by flash chromatography (silica gel) using 10% EtOAc in hexane to afford the title compound as a brown semi-solid (0.4 g, 60%). The reaction mixture is purged with nitrogen for 5 minutes the reaction is cooled to ambient temperature filtered through Celite™ washed with EtOAc The combined filtrates are dried over sodium sulfate filtered concentrated under reduced pressure purified by flash chromatography (silica gel)

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

Procedure: Dissolve lauric acid (0.77 g) in methylene chloride (50mL) and cool to 0° C. Add oxalyl chloride (0.37 mL) and dimethylformamide (3 drops). Allow to warm to room temperature and stir for 1 hour. Add, by dropwise addition, to a solution of 3-(O-tert-butyldimethylsilyloxy)piperidine (0.76 g, 3.5 mmol) and triethylamine (1 mL) in methylene chloride (20 mL). Stir overnight. Dilute with methylene chloride (50 mL) and separate the organic phase. Wash twice with 10% sodium hydroxide, once with 10% hydrochloric acid, and once with saturated sodium hydrogen carbonate and once with brine. Dry (Na2SO4) and evaporate the solvent in vacuo to give 1-oxododecyl-3-(O-tert-butyldimethylsilyoxy)piperidine. Allow to warm to room temperature Stir overnight separate the organic phase Wash twice with 10% sodium hydroxide, once with 10% hydrochloric acid Dry (Na2SO4) evaporate the solvent in vacuo

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 3-[(5-bromo-2-methyl-benzoyl)amino]-2,4-dimethyl-benzoate (0.5 g, 1.32 mmol), tert-butyl-dimethyl-(3-piperidyloxy)silane (0.425 g, 1.98 mmol) and Cs2CO3 (1.28 g, 3.96 mmol) in 1,4-dioxane (15 ml) is added Pd2(dba)3 (0.12 g, 0.132 mmol) followed by S-Phos (0.054 g, 0.132 mmol). The reaction mixture is purged with nitrogen for 5 minutes and then heated at 100° C. After 16 hours, the reaction is cooled to ambient temperature, filtered through Celite™, and washed with EtOAc. The combined filtrates are dried over sodium sulfate, filtered, and concentrated under reduced pressure and purified by flash chromatography (silica gel) using 10% EtOAc in hexane to afford the title compound as a brown semi-solid (0.4 g, 60%). The reaction mixture is purged with nitrogen for 5 minutes the reaction is cooled to ambient temperature filtered through Celite™ washed with EtOAc The combined filtrates are dried over sodium sulfate filtered concentrated under reduced pressure purified by flash chromatography (silica gel)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 3-[(5-bromo-2-methyl-benzoyl)amino]-2,4-dimethyl-benzoate (0.5 g, 1.32 mmol), tert-butyl-dimethyl-(3-piperidyloxy)silane (0.425 g, 1.98 mmol) and Cs2CO3 (1.28 g, 3.96 mmol) in 1,4-dioxane (15 ml) is added Pd2(dba)3 (0.12 g, 0.132 mmol) followed by S-Phos (0.054 g, 0.132 mmol). The reaction mixture is purged with nitrogen for 5 minutes and then heated at 100° C. After 16 hours, the reaction is cooled to ambient temperature, filtered through Celite™, and washed with EtOAc. The combined filtrates are dried over sodium sulfate, filtered, and concentrated under reduced pressure and purified by flash chromatography (silica gel) using 10% EtOAc in hexane to afford the title compound as a brown semi-solid (0.4 g, 60%). The reaction mixture is purged with nitrogen for 5 minutes the reaction is cooled to ambient temperature filtered through Celite™ washed with EtOAc The combined filtrates are dried over sodium sulfate filtered concentrated under reduced pressure purified by flash chromatography (silica gel)