반응 #44989

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Trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid

dimethylamine hydrochloride

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

triethylamine

→

methyl trans-4-[(dimethylamino)carbonyl]-cyclohexanecarboxylate

수율 87.7%

용매

chloroform

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후처리

1. 1
   온도cooling
2. 2
   추출the mixture is extracted with chloroform
3. 3
   세척The organic layer is washed with 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine successively
4. 4
   건조dried over sodium sulfate
5. 5
   농축The solvent is concentrated under reduced pressure
6. 6
   기타the resulting residue is purified by silica gel column chromatography (eluent: chloroform, followed by chloroform/methanol=20/1)

실험 절차

Trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (20.0 g) obtained in Reference Example 1(2) is dissolved in chloroform (200 ml), and thereto are added dimethylamine hydrochloride (10.5 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (24.7 g) and triethylamine (26.0 g) under ice-cooling. The mixture is then stirred at room temperature for 17 hours. Ice-water is poured to the reaction solution and the mixture is extracted with chloroform. The organic layer is washed with 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine successively and dried over sodium sulfate. The solvent is concentrated under reduced pressure and the resulting residue is purified by silica gel column chromatography (eluent: chloroform, followed by chloroform/methanol=20/1) to give methyl trans-4-[(dimethylamino)carbonyl]-cyclohexanecarboxylate (20.1 g).

출처