Ethyl 1-cyanocyclopropanecarboxylate → Ethyl 1-(aminomethyl)cyclopropanecarboxylate

HRID 1055902

Reaktionsgleichung

Reaktionsgleichung von HRID 1055902
[C:1]([C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1)#[N:2]>[Ni].CO>[NH2:2][CH2:1][C:3]1([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4]1

Komponenten

4

Edukt 1

HCID 380810Ethyl 1-cyanocyclopropanecarboxylate

Produkt 1

HCID 11480505Ethyl 1-(aminomethyl)cyclopropanecarboxylateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

In a 500-mL Parr shaker vessel, Raney nickel (750 mg) was added to MeOH (30 mL). Ethyl 1-cyanocyclopropanecarboxylate (Aldrich; 2.0 g, 14.38 mmol) was added and the resulting mixture was shaken vigorously under an H2 atmosphere (50 psi) for 24 h. The mixture was subsequently filtered through Celite, washing the Celite pad with MeOH (2×20 mL). The combined filtrates were concentrated in vacuo to provide ethyl 1-(aminomethyl)cyclopropanecarboxylate (1.5 g, 10.48 mmol, 73% yield): 1H NMR (400 MHz, CDCl3): δ 4.13 (q, 2H, J=7.2 Hz), 3.67 (s, 1H), 3.44 (s, 1H), 2.74 (br s, 2H), 1.27-1.21 (m, 5H), 0.80-0.74 (m, 2H). m/z (ESI, +ve) 144.4 (M+H)+.

Aufarbeitung

  1. filtrationThe mixture was subsequently filtered through Celite
  2. washwashing the Celite pad with MeOH (2×20 mL)
  3. concentrationThe combined filtrates were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9fbd0ac739544c4fb347fef82b7dc619
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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