反応 #44989

反応方程式

Trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid

dimethylamine hydrochloride

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

triethylamine

→

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

収率 87.7%

溶媒

chloroform

反応条件

後処理

1. 1
   温度cooling
2. 2
   抽出the mixture is extracted with chloroform
3. 3
   洗浄The organic layer is washed with 10% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine successively
4. 4
   乾燥dried over sodium sulfate
5. 5
   濃縮The solvent is concentrated under reduced pressure
6. 6
   その他the resulting residue is purified by silica gel column chromatography (eluent: chloroform, followed by chloroform/methanol=20/1)

実験手順

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).

出典