Reaktion #429229

Reaktionsgleichung

hydrochloric acid

potassium cyanide

(S)-1-phenylpropylamine

ethyl 1-formylcyclopropane-1-carboxylate

→

diastereomer mixture

Ausbeute 59.1%

1-[(RS)-1-Cyano-[(S)-1-phenylpropylamino]methyl]-1-ethoxycarbonylcyclopropane

Ausbeute 59.1%

Lösungsmittel

ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITfor 2 hours at 50° C
2. 2
   Sonstigecompletion of the reaction
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenNext, the resulting organic layer was washed with water and saturated brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Sonstigeafter removing insoluble matter
7. 7
   Filtrationby filtration
8. 8
   Sonstigethe solvent was evaporated under a reduced pressure

Vorschrift

An eggplant type flask was charged with 136 mg of potassium cyanide, 501 mg of (S)-1-phenylpropylamine and 1 ml of water. After adding 152 mg of ethyl 1-formylcyclopropane-1-carboxylate dissolved in 2 ml of ethanol, dropwise at room temperature, the resulting mixture was further mixed with 0.2 ml of concentrated hydrochloric acid, and stirred for 1 hour at the same temperature and then for 2 hours at 50° C. After confirming completion of the reaction, the reaction solution was mixed with ice water and extracted with ethyl acetate. Next, the resulting organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate and, after removing insoluble matter by filtration, the solvent was evaporated under a reduced pressure. Thereafter, the resulting residue was subjected to a silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 181 mg (59%) of a diastereomer mixture in the form of colorless oil. Formation ratio of the two diastereomers was calculated under the following analytical conditions.

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