Methyl 1-cyanocyclopentane-1-carboxylate → Methyl 1-(aminomethyl)cyclopentanecarboxylate

HRID 51068Notes

Reaction equation

HRID 51068 reaction equation
[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]1

Participants

4

Reactant 1

HCID 22736532Methyl 1-cyanocyclopentane-1-carboxylate

Product 1

HCID 13285792Methyl 1-(aminomethyl)cyclopentanecarboxylate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  1. additionThe reaction was charged with H2 at 50 psi
  2. customThe RaNi catalyst was removed by filtration through a layer of celite
  3. customThe solvent was removed under vacuum
  4. dissolutionThe crude product was dissolved in 1N NaHSO4 (100 mL)
  5. washwashed with Et2O (2×100 mL)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-eea42df30e8e4af9b832489391d5aecd
Source dataset
uspto-grants-2004_03
Patent number
US06713476B2

Reaction notes

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