methyl 2-(benzylamino)-2-phenylacetate

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

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

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

Procedure: A solution of methyl 2-(benzylamino)-2-phenylacetate (1.00 g, 3.90 mmol) in THF (90 ml) and 1N NaOH (10 ml) was stirred at room temperature overnight (LC-MS monitoring: complete conversion). The solvent was removed under reduced pressure, and the crude product was partitioned between EtOAc and water. The aqueous phase was acidified with conc. HCl (pH about 3) and then extracted with EtOAc (three times). The organic phase was dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a white solid (940 mg, quantitative yield), which is used in the next step without any further purification. The solvent was removed under reduced pressure the crude product was partitioned between EtOAc and water extracted with EtOAc (three times) The organic phase was dried over Na2SO4 filtered evaporated to dryness

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

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 2-(benzylamino)-2-phenylacetate (4.818 g, 18.9 mmol) and pyridine (15.3 ml, 189 mmol) in 75 mL dichloromethane cooled by an ice bath was added 4-nitrobenzoyl chloride (3.50 g, 18.9 mmol) all at once. The cold bath was removed and the reaction stirred to room temperature. The reaction was stirred at room temperature for four hours then concentrated under reduced pressure, taken up in 100 mL heptane and concentrated under reduced pressure. The concentrate was partitioned between 100 mL dichloromethane and 100 mL water. The organic separation was washed with 50 mL brine then stirred over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a colorless oil. The product was purified by chromatography on silica, eluting with 10-30% ethyl acetate in hexane to afford a colorless foamy solid (7.37 g, 96%). ESI+ m/z=405.1 [MH]+. The cold bath was removed The reaction was stirred at room temperature for four hours then concentrated under reduced pressure concentrated under reduced pressure The concentrate was partitioned between 100 mL dichloromethane and 100 mL water The organic separation was washed with 50 mL brine then stirred over magnesium sulfate filtered the filtrate concentrated under reduced pressure to afford a colorless oil The product was purified by chromatography on silica eluting with 10-30% ethyl acetate in hexane

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

Procedure: to a mixture of benzaldehyde (3.06 ml, 30.3 mmol) and methyl 2-amino-2-phenylacetate 1a (4.552 g, 27.6 mmol) in 50 mL 1,2-dichloroethane was added sodium triacetoxyborohydride (14.6 g, 68.9 mmol) all at once. The reaction mixture was stirred at room temperature for several hours then poured into 100 mL saturated aqueous sodium bicarbonate solution. The biphase was vigorously stirred for 15 minutes then the organic separation dried over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a colorless oil. The product was purified by chromatography on silica gel eluting with 10-40% ethyl acetate in hexane. ESI+ m/z=256.1 [MH]+. The biphase was vigorously stirred for 15 minutes the organic separation dried over magnesium sulfate filtered the filtrate concentrated under reduced pressure to afford a colorless oil The product was purified by chromatography on silica gel eluting with 10-40% ethyl acetate in hexane

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

Procedure: A solution of methyl 2-(benzylamino)-2-phenylacetate (1.00 g, 3.90 mmol) in THF (90 mL) and 1N NaOH (10 mL) is stirred at room temperature overnight (LC-MS monitoring: complete conversion). The solvent is removed under reduced pressure and the crude is portioned between EtOAc and water. The aqueous phase is acidified with conc. HCl (pH about 3) and then extracted with EtOAc (three times). The organic phase is dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a white solid (940 mg, quantitative yield), which is used in the next step without any further purification. The solvent is removed under reduced pressure extracted with EtOAc (three times) The organic phase is dried over Na2SO4 filtered evaporated to dryness

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

Procedure: A solution of methyl 2-(benzylamino)-2-phenylacetate (1.00 g, 3.90 mmol) in THF (90 mL) and 1N NaOH (10 mL) is stirred at room temperature overnight (LC-MS monitoring: complete conversion). The solvent is removed under reduced pressure and the crude is portioned between EtOAc and water. The aqueous phase is acidified with conc. HCl (pH about 3) and then extracted with EtOAc (three times). The organic phase is dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a white solid (940 mg, quantitative yield), which is used in the next step without any further purification. The solvent is removed under reduced pressure extracted with EtOAc (three times) The organic phase is dried over Na2SO4 filtered evaporated to dryness

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

Procedure: A solution of methyl 2-(benzylamino)-2-phenylacetate (1.00 g, 3.90 mmol) in THF (90 ml) and 1N NaOH (10 ml) was stirred at room temperature overnight (LC-MS monitoring: complete conversion). The solvent was removed under reduced pressure, and the crude product was partitioned between EtOAc and water. The aqueous phase was acidified with conc. HCl (pH about 3) and then extracted with EtOAc (three times). The organic phase was dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a white solid (940 mg, quantitative yield), which is used in the next step without any further purification. The solvent was removed under reduced pressure the crude product was partitioned between EtOAc and water extracted with EtOAc (three times) The organic phase was dried over Na2SO4 filtered evaporated to dryness