Reaktion #1162879

Reaktionsgleichung

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

Lösungsmittel

chloroform

methylene chloride

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

(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).

Quelle