反応 #8221

反応方程式

[2-(7-hydroxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester

dimethylformamide

sodium hydride

methyl-2-chloroacetate

→

[2-(7-(methoxycarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester

収率 30.0%

反応条件

後処理

1. 1
   workup.ADDITIONadded portion-wise over a 10 minute period
2. 2
   温度The mixture is cooled in an ice/water bath
3. 3
   その他The ice bath is removed
4. 4
   その他The reaction is then quenched with saturated brine
5. 5
   抽出extracted with ethyl acetate
6. 6
   乾燥The ethyl acetate layer is dried
7. 7
   濃縮concentrated
8. 8
   その他to give a crude residue, which
9. 9
   その他is purified by silica gel chromatography (gradient elution, chloroform with 1%–10% of 20% methanol in acetonitrile)

実験手順

A solution of [2-(7-hydroxy-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (609 mg, 2.0 mmol) is dissolved in dry dimethylformamide (30 ml) under a nitrogen atmosphere and treated with sodium hydride (84 mg, 2.1 mmol, 60% dispersion in oil) added portion-wise over a 10 minute period. The mixture is cooled in an ice/water bath and methyl-2-chloroacetate (434 mg, 4.0 mmol) is added drop-wise over 20 minutes. The ice bath is removed and the mixture stirred at room temperature for 15 hours. The reaction is then quenched with saturated brine and extracted with ethyl acetate. The ethyl acetate layer is dried and concentrated to give a crude residue, which is purified by silica gel chromatography (gradient elution, chloroform with 1%–10% of 20% methanol in acetonitrile) to give 230 mg of [2-(7-(methoxycarbomethoxy)-1H-indol-3-yl)-1,1-dimethyl-ethyl]-carbamic acid tert-butyl ester (30%).

出典