Reacción #41289

Ecuación de reacción

N2-(tert-butoxycarbonyl)-N-methoxy-N-methyl-L-alaninamide

bromo(3-methoxyphenyl)magnesium

→

subtitle compound

tert-Butyl[(1S)-2-(3-methoxyphenyl)-1-methyl-2-oxoethyl]carbamate

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with saturated aqueous NH4Cl (50 ml)
2. 2
   workup.STIRRINGAfter stirring for 30 min
3. 3
   Otrothe layers were separated
4. 4
   Extracciónthe aqueous layer extracted with ethyl acetate (50 ml)
5. 5
   SecadoThe combined organic layers were dried with Na2SO4
6. 6
   Otrothe solvent was removed in vacuo

Procedimiento

To a stirred solution of N2-(tert-butoxycarbonyl)-N-methoxy-N-methyl-L-alaninamide (777 mg, 3.3 mmol) in dry THF (50 ml) was added a solution of bromo(3-methoxyphenyl)magnesium (1M in THF, 10 ml, 10 mmol). The mixture was stirred at r.t. for 5 h, then quenched with saturated aqueous NH4Cl (50 ml). After stirring for 30 min, the layers were separated, the aqueous layer extracted with ethyl acetate (50 ml). The combined organic layers were dried with Na2SO4, and the solvent was removed in vacuo. The subtitle compound was isolated by flash chromatography on silica gel (n-heptane/ethyl acetate, gradient from 20 to 50% ethyl acetate). Yield 471 mg (94%).

Fuente