تفاعل #41289

معادلة التفاعل

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

المذيبات

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر