Benzylamine → 1-(1-Benzylamino-1-cyanomethyl)-1-ethoxycarbonylcyclopropane

HRID 342041

Reaktionsgleichung

Reaktionsgleichung von HRID 342041
[CH:1]([C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1)=O.S([O-])(O)=O.[Na+].[C-:16]#[N:17].[K+].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C.O>[CH2:19]([NH:26][CH:1]([C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1)[C:16]#[N:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

7

Edukt 4

HCID 7504BenzylamineHCID 9032Potassium CyanideHCID 9964122Ethyl 1-formylcyclopropanecarboxylateHCID 23665763Sodium Bisulfite

Produkt 1

HCID 153910461-(1-Benzylamino-1-cyanomethyl)-1-ethoxycarbonylcyclopropaneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

An eggplant type flask was charged with 501 mg of ethyl 1-formylcyclopropane-1-carboxylate and 2 ml of water to which were further added 1.13 g of sodium hydrogen sulfite and 345 mg of potassium cyanide. Thereto was added dropwise 564 mg of benzylamine dissolved in 5 ml of ethanol at room temperature, followed by 2.5 hours of stirring the reaction solution 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 saturated brine, dried over anhydrous magnesium sulfate and, after removing insoluble matter by filtration, concentrated under a reduced pressure. Thereafter, the resulting residue was subjected to a silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 717 mg (79%) of the title compound in the form of colorless oil. Spectrum data of the thus obtained oily product coincided with those of the compound of Inventive Example 2.

Aufarbeitung

  1. customcompletion of the reaction
  2. extractionextracted with ethyl acetate
  3. washNext, the resulting organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter removing insoluble matter
  6. filtrationby filtration
  7. concentrationconcentrated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aa72cbc4646e4f62a6622ce558e7dbc7
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856518

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