Methyl 1-cyanocyclopentane-1-carboxylate → Methyl 1-(aminomethyl)cyclopentanecarboxylate
Reaktionsgleichung
[C:1]([C:3]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2]>CO.[Ni]>[NH2:2][CH2:1][C:3]1([C:8]([O:10][CH3:11])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of methyl 1-cyanocyclopentanecarboxylate (15 g, 98 mmol) in MeOH (250 mL) was added RaNi (3 g). The reaction was charged with H2 at 50 psi and shaken in the Parr shaker for 24 h. The RaNi catalyst was removed by filtration through a layer of celite. The solvent was removed under vacuum. The crude product was dissolved in 1N NaHSO4 (100 mL) and then washed with Et2O (2×100 mL). The organic layer was dried over magnesium sulfate and then filtered. The solvents were removed under reduced pressure to provide the amine in 77%; 1H NMR (300 MHz, CD3OD) δ3.75 (s, 3H), 3.12 (s, 2H), 2.14×2.07 (m, 2H), 1.83×1.65 (m, 6H). MS [M+H]+470.