反応 #41293

反応方程式

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

magnesium

1-bromo-4-ethylbenzene

iodine

→

subtitle compound

tert-Butyl[(1S)-2-(4-ethylphenyl)-1-methyl-2-oxoethyl]carbamate

溶媒

THF

THF

THF

反応条件

後処理

1. 1
   温度The reaction mixture was heated
2. 2
   温度with reflux for 4 h
3. 3
   その他Then the reaction mixture was quenched with sat. aqueous NH4Cl (25 ml)
4. 4
   その他the layers were separated
5. 5
   抽出The aqueous layer extracted with ethyl acetate (50 ml)
6. 6
   乾燥The combined organic layers were dried with Na2SO4
7. 7
   その他the solvent was removed under reduced pressure

実験手順

To a stirred suspension of magnesium turnings (243 mg, 10 mmol) in dry THF (10 ml) was added a solution of 1-bromo-4-ethylbenzene (1.85 g, 10 mmol) in dry THF (10 ml), followed by a small crystal of iodine. The reaction mixture was heated with reflux for 4 h, then cooled to r.t. A solution of N2-(tert-butoxycarbonyl)-N-methoxy-N-methyl-L-alaninamide (464 mg, 2 mmol) in dry THF (15 ml) was added dropwise, and the stirring was continued for 5 h at r.t. Then the reaction mixture was quenched with sat. aqueous NH4Cl (25 ml) stirred for 30 min, and 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 under reduced pressure to give the subtitle compound as colourless oil, 718 mg, 70% purity (as determined by NMR). Used in the next step without further purification.

出典