ethyl 2-[(1S)-1-phenylethyl]iminoacetate

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The synthesis was performed according to the procedure reported in the literature. (S)-(−)-α-Methylbenzylamine (238.6 g, 1.964 mol) was added into 2 L round bottom flask equipped a stirrer bar. Toluene (520 mL) was added. The reaction mixture was cooled to −5° C., and was allowed to stir for 10 min. Glyoxylic acid (200 g, 1.96 mol) was tranferred to a dropping funnel and was added slowly to the cooled reaction mixture for approximately 15 min. As the addition of the glyoxylic acid proceeded, the reaction mixture became cloudy and the flask became warm. The mixture was allowed to stir for 10 min after the addition. When the reaction was complete, the water generated during the reaction was removed. The organic layer was dried over Na2SO4, filtered via Buchner funnel, rinsed with toluene, concentrated in vacuo to yield an oil which was used directly in the next step. equipped a stirrer bar was added slowly to the cooled reaction mixture for approximately 15 min the flask became warm to stir for 10 min after the addition was removed The organic layer was dried over Na2SO4 filtered via Buchner funnel rinsed with toluene concentrated in vacuo to yield an oil which

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The synthesis was performed according to the procedure reported in the literature. (S)-(−)-α-Methylbenzylamine (238.6 g, 1.964 mol) was added into 2 L round bottom flask equipped a stirrer bar. Toluene (520 mL) was added. The reaction mixture was cooled to −5° C., and was allowed to stir for 10 min. Glyoxylic acid (200 g, 1.96 mol) was tranferred to a dropping funnel and was added slowly to the cooled reaction mixture for approximately 15 min. As the addition of the glyoxylic acid proceeded, the reaction mixture became cloudy and the flask became warm. The mixture was allowed to stir for 10 min after the addition. When the reaction was complete, the water generated during the reaction was removed. The organic layer was dried over Na2SO4, filtered via Buchner funnel, rinsed with toluene, concentrated in vacuo to yield an oil which was used directly in the next step. equipped a stirrer bar was added slowly to the cooled reaction mixture for approximately 15 min the flask became warm to stir for 10 min after the addition was removed The organic layer was dried over Na2SO4 filtered via Buchner funnel rinsed with toluene concentrated in vacuo to yield an oil which

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

Procedure: Treat a solution of neat (S)-α-methylbenzylamine (7.5 mL, 59 mmol) in dichloromethane (300 mL) at 0° C. with ethyl glyoxalate solution (50% in toluene, 11.5 mL). Add 4Å molecular sieves (20 g) to the above solution. Stir the reaction mixture at 0° C. for 2 h. Filter the solids off, concentrate and purify (silica gel chromatography, eluting with 20:80 to 70:30 ethyl acetate:hexanes) to give the title compound (11.1 g, 97%) Add 4Å molecular sieves (20 g) to the above solution Filter the solids off, concentrate purify (silica gel chromatography, eluting with 20:80 to 70:30 ethyl acetate:hexanes)