methyl 2-amino-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:

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

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