反応 #1162879

反応方程式

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

2-hydroxy-n-octanoic acid

N-hydroxysuccinimide

morpholine

→

(1S,2S)-2-Amino-3-morpholino-1-phenyl-1-propanol

溶媒

chloroform

methylene chloride

反応条件

後処理

1. 1
   その他The compound obtained (99.2 mg, 0.42 mmol)
2. 2
   workup.ADDITIONwas added
3. 3
   洗浄the resulting organic layer was washed with a 5% citric acid solution
4. 4
   乾燥a saturated sodium bicarbonate solution and water in this order, dried over anhydrous sodium sulfate
5. 5
   ろ過filtered
6. 6
   その他The solvent was removed by evaporation
7. 7
   その他the resulting residue was purified by silica gel column chromatography (ethyl acetate)
8. 8
   その他to obtain the objective compound as a colorless oily material as one of its diastereomer (15.4 mg)

実験手順

(1S,2S)-2-Amino-3-morpholino-1-phenyl-1-propanol was prepared in the same manner as in Example 11, except that morpholine was used in place of N-methylpiperazine. The compound obtained (99.2 mg, 0.42 mmol) was dissolved in methylene chloride, 2-hydroxy-n-octanoic acid (80.0 mg, 0.50 mmol) and N-hydroxysuccinimide (102.1 mg, 0.42 mmol) were added thereto at room temperature, and then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (118.1 mg, 0.62 mmol) was added thereto under ice cooling and further stirred. After completion of the reaction, chloroform was added thereto and the resulting organic layer was washed with a 5% citric acid solution, a saturated sodium bicarbonate solution and water in this order, dried over anhydrous sodium sulfate and then filtered. The solvent was removed by evaporation, and the resulting residue was purified by silica gel column chromatography (ethyl acetate) to obtain the objective compound as a colorless oily material as one of its diastereomer (15.4 mg), as well as the other diastereomer (16.9 mg).

出典