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

HRID 342047

Reaktionsgleichung

Reaktionsgleichung von HRID 342047
[C-:1]#[N:2].[K+].[C:4]1([C@@H:10]([NH2:13])[CH2:11][CH3:12])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:14]([C:16]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17]1)=O.Cl>C(O)C.O>[C:1]([CH:14]([NH:13][C@H:10]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:11][CH3:12])[C:16]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17]1)#[N:2]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 6993773(1S)-1-phenylpropan-1-amineHCID 9964122Ethyl 1-formylcyclopropanecarboxylate

Produkt 1

HCID 702112091-[(RS)-1-Cyano-[(S)-1-phenylpropylamino]methyl]-1-ethoxycarbonylcyclopropaneAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. waitfor 2 hours at 50° C
  2. customcompletion of the reaction
  3. extractionextracted with ethyl acetate
  4. washNext, the resulting organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter removing insoluble matter
  7. filtrationby filtration
  8. customthe solvent was evaporated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d5a95cc5e12c49ebb314619c0387ebd4
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856518

Verknüpfte Notizen

Wird geladen…