반응 #1162879

반응 방정식

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

용매

chloroform

methylene chloride

반응 조건

후처리

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

실험 절차

(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).

출처