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

HRID 2234512Notes

Reaction equation

HRID 2234512 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:10]#[N:11])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]>C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1([CH2:10][NH2:11])[CH2:6][CH2:7][CH2:8][CH2:9]1)=[O:4]

Participants

3

Reactant 1

HCID 22736532Methyl 1-cyanocyclopentane-1-carboxylate2×

Product 1

HCID 13285792Methyl 1-(aminomethyl)cyclopentanecarboxylateYield 100.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl1-cyanocyclopentane-1-carboxylate (Intermediate 260; 6 g, 39.2 mmol) in acetic acid (70 mL) was hydrogenated using Pt O2 (600 mg) as a catalyst at room temperature under 4 Bar pressure for 4 hours. The reaction mixture was filtered and concentrated. The residue was taken up in methanol and absorbed on to an SCX column (3×50 g), which was then washed with methanol and eluted with ammonia in methanol. Concentration of product containing fractions yielded the title compound as a pale yellow liquid (6.18 g, 100%).

Workup

  1. customat room temperature
  2. customfor 4 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. customabsorbed on to an SCX column (3×50 g), which
  6. washwas then washed with methanol
  7. washeluted with ammonia in methanol
  8. additionConcentration of product containing fractions

Sources & evidence

ORD record
ord-7291eb837dae4ec89eec34d474cecb2e
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

Loading…