N-benzyl-2-phenylacetamide

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

Procedure: Into a 25 mL round bottom flask equipped with a stir bar was added phenyl acetic acid (0.075 g, 0.55 mmol, 1.1 equiv), (2-iodo-5-methoxyphenyl)boronic acid (13.9 mg, 0.05 mmol, 10 mol %) and 1 g of activated 4 Å Molecular Sieves. Dichloromethane (7 mL) was added and the mixture was stirred for 10 min. Then, benzylamine (55 pit, 0.5 mmol, 1 equiv) was added (in order to get reproducible results, it is necessary to use a gas tight 100 μL syringe). The resulting mixture was stirred for 2 h at room temperature (24-25° C.). The reaction mixture was filtered through a pad of Celite® 545, the filtrate was washed with aqueous acidic solution (pH=4), aqueous basic solution (pH=10-11) and brine. The organic layer was collected, dried over anhydrous Na2SO4 and evaporated to yield the title compound (71% using 1, 98% using 2) as a pure product. The catalyst can be recuperated in up to 80% yield by acidification of the aqueous basic solution to pH 7 and extraction with EtOAc. Into a 25 mL round bottom flask equipped with a stir bar (in order to get reproducible results, it is necessary to use a gas tight 100 μL syringe) The resulting mixture was stirred for 2 h at room temperature (24-25° C.) The reaction mixture was filtered through a pad of Celite® 545 the filtrate was washed with aqueous acidic solution (pH=4), aqueous basic solution (pH=10-11) and brine The organic layer was collected dried over anhydrous Na2SO4 evaporated

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

Procedure: Into a 25 mL round bottom flask equipped with a stir bar was added phenyl acetic acid (0.075 g, 0.55 mmol, 1.1 equiv), (2-iodo-5-methoxyphenyl)boronic acid (13.9 mg, 0.05 mmol, 10 mol %) and 1 g of activated 4 Å Molecular Sieves. Dichloromethane (7 mL) was added and the mixture was stirred for 10 min. Then, benzylamine (55 pit, 0.5 mmol, 1 equiv) was added (in order to get reproducible results, it is necessary to use a gas tight 100 μL syringe). The resulting mixture was stirred for 2 h at room temperature (24-25° C.). The reaction mixture was filtered through a pad of Celite® 545, the filtrate was washed with aqueous acidic solution (pH=4), aqueous basic solution (pH=10-11) and brine. The organic layer was collected, dried over anhydrous Na2SO4 and evaporated to yield the title compound (71% using 1, 98% using 2) as a pure product. The catalyst can be recuperated in up to 80% yield by acidification of the aqueous basic solution to pH 7 and extraction with EtOAc. Into a 25 mL round bottom flask equipped with a stir bar (in order to get reproducible results, it is necessary to use a gas tight 100 μL syringe) The resulting mixture was stirred for 2 h at room temperature (24-25° C.) The reaction mixture was filtered through a pad of Celite® 545 the filtrate was washed with aqueous acidic solution (pH=4), aqueous basic solution (pH=10-11) and brine The organic layer was collected dried over anhydrous Na2SO4 evaporated

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

Procedure: The iodo derivative 53 was hydrolysed as described under general procedures to give the title compound as an orange colored powder in quantitative yield. Reaction of dimethyl phenylacetylphosphonate (50b) with benzylamine To a solution of the phosphonate 50b in CHCl3 (5 ml) was added molecular sieves (4A, 0.25 g) followed by benzylamine (0.11 g, 1 mmol). After 0.5 h a catalytic amount of TsOH was added and the mixture was stirred for 2 h. The mixture was filtered and flash chromatography (silica, 3:7 EtOAc/hexane) of the filtrate provided N-benzylphenylacetamide (61), as determined by comparison with an authentic sample. The mixture was filtered

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

Procedure: Into a 25 mL round bottom flask equipped with a stir bar was added phenyl acetic acid (0.075 g, 0.55 mmol, 1.1 equiv), (2-iodo-5-methoxyphenyl)boronic acid (13.9 mg, 0.05 mmol, 10 mol %) and 1 g of activated 4 Å Molecular Sieves. Dichloromethane (7 mL) was added and the mixture was stirred for 10 min. Then, benzylamine (55 pit, 0.5 mmol, 1 equiv) was added (in order to get reproducible results, it is necessary to use a gas tight 100 μL syringe). The resulting mixture was stirred for 2 h at room temperature (24-25° C.). The reaction mixture was filtered through a pad of Celite® 545, the filtrate was washed with aqueous acidic solution (pH=4), aqueous basic solution (pH=10-11) and brine. The organic layer was collected, dried over anhydrous Na2SO4 and evaporated to yield the title compound (71% using 1, 98% using 2) as a pure product. The catalyst can be recuperated in up to 80% yield by acidification of the aqueous basic solution to pH 7 and extraction with EtOAc. Into a 25 mL round bottom flask equipped with a stir bar (in order to get reproducible results, it is necessary to use a gas tight 100 μL syringe) The resulting mixture was stirred for 2 h at room temperature (24-25° C.) The reaction mixture was filtered through a pad of Celite® 545 the filtrate was washed with aqueous acidic solution (pH=4), aqueous basic solution (pH=10-11) and brine The organic layer was collected dried over anhydrous Na2SO4 evaporated