Reaktion #41289

Reaktionsgleichung

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle