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

HRID 1055902

Reaction equation

HRID 1055902 reaction equation
[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

Participants

4

Reactant 1

HCID 380810Ethyl 1-cyanocyclopropanecarboxylate

Product 1

HCID 11480505Ethyl 1-(aminomethyl)cyclopropanecarboxylateYield 73%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-9fbd0ac739544c4fb347fef82b7dc619
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Linked notes

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