ethyl 1-cyanocyclobutanecarboxylate → Ethyl 1-(aminomethyl)cyclobutanecarboxylate

HRID 2242384Notes

Reaction equation

HRID 2242384 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:10]#[N:11])[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[H][H]>C(O)C.[Ni].O>[CH2:1]([O:3][C:4]([C:6]1([CH2:10][NH2:11])[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 275343ethyl 1-cyanocyclobutanecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 45122079Ethyl 1-(aminomethyl)cyclobutanecarboxylateYield 72%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

1-Cyano-cyclobutanecarboxylic acid ethyl ester (2.00 g, 13.0 mmol) was dissolved in ethanol (30 ml) and treated with Raney Nickel (1 ml as a slurry in water) and hydrogen gas at 4 bar and heating at 40° C. for 18 h. The reaction mixture was filtered through Dicalite and washed through with ethanol (50 ml). The solvent was removed under reduced pressure to give 1-aminomethyl-cyclobutanecarboxylic acid ethyl ester as a yellow oil (1.47 g, 72%).

Workup

  1. filtrationThe reaction mixture was filtered through Dicalite
  2. washwashed through with ethanol (50 ml)
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a44dee56808f4538984451ebc3637586
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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