تفاعل #41293

معادلة التفاعل

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

المذيبات

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was heated
2. 2
   درجة الحرارةwith reflux for 4 h
3. 3
   أخرىThen the reaction mixture was quenched with sat. aqueous NH4Cl (25 ml)
4. 4
   أخرىthe layers were separated
5. 5
   استخلاصThe aqueous layer extracted with ethyl acetate (50 ml)
6. 6
   تجفيفThe combined organic layers were dried with Na2SO4
7. 7
   أخرىthe solvent was removed under reduced pressure

الإجراء التجريبي

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.

المصدر