methyl 4-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]benzoate

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

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

Procedure: To a solution of methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate (3.50 g, 12.5 mmol) in methylene chloride (35 ml) was added 4N hydrogen chloride in 1,4-dioxane (35 ml) at 5° C. and the mixture was stirred for 30 min. The solvent was removed in vacuo and the resulting solid was collected, washed with isopropyl ether and dried to give methyl 4-(2-aminoethyl)-benzoate hydrochloride (2.63 g, 97%). The solvent was removed in vacuo the resulting solid was collected washed with isopropyl ether dried

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

Procedure: To a solution of methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate (3.50 g, 12.5 mmol) in methylene chloride (35 ml) was added 4N hydrogen chloride in 1,4-dioxane (35 ml) at 5° C. and the mixture was stirred for 30 min. The solvent was removed in vacuo and the resulting solid was collected, washed with isopropyl ether and dried to give methyl 4-(2-aminoethyl)-benzoate hydrochloride (2.63 g, 97%). The solvent was removed in vacuo the resulting solid was collected washed with isopropyl ether dried

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

Procedure: A mixture of 4-[2-(tert-butoxycarbonylamino)ethyl]-phenyl trifluoromethanesulfonate (6.11 g, 16.6 mmol), palladium(II) acetate (745 mg, 3.32 mmol), 1,3-bis-(diphenylphosphino)propane (1.37 g, 3.32 mmol), triethylamine (6.94 ml, 49.8 mmol), and MeOH (24ml) in DMF (60 ml) was purged for 30 min with carbon monoxide. The mixture was stirred under carbon monoxide atmosphere at 78° C. for 3 hours. After cooling the mixture to room temperature, the reaction mixture was diluted with EtOAc, washed with water, 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate, water and brine successively, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:EtOAc, 4:1-3:1) to give methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate (3.52 g, 76%). was purged for 30 min with carbon monoxide After cooling the mixture to room temperature the reaction mixture was diluted with EtOAc washed with water, 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate, water and brine successively dried over magnesium sulfate evaporated in vacuo The residue was purified by silica gel column chromatography (hexane:EtOAc, 4:1-3:1)

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

Procedure: A mixture of 4-[2-(tert-butoxycarbonylamino)ethyl]-phenyl trifluoromethanesulfonate (6.11 g, 16.6 mmol), palladium(II) acetate (745 mg, 3.32 mmol), 1,3-bis-(diphenylphosphino)propane (1.37 g, 3.32 mmol), triethylamine (6.94 ml, 49.8 mmol), and MeOH (24ml) in DMF (60 ml) was purged for 30 min with carbon monoxide. The mixture was stirred under carbon monoxide atmosphere at 78° C. for 3 hours. After cooling the mixture to room temperature, the reaction mixture was diluted with EtOAc, washed with water, 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate, water and brine successively, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:EtOAc, 4:1-3:1) to give methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate (3.52 g, 76%). was purged for 30 min with carbon monoxide After cooling the mixture to room temperature the reaction mixture was diluted with EtOAc washed with water, 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate, water and brine successively dried over magnesium sulfate evaporated in vacuo The residue was purified by silica gel column chromatography (hexane:EtOAc, 4:1-3:1)