Methyl 1-cyanocyclopentane-1-carboxylate → Methyl 1-(aminomethyl)cyclopentanecarboxylate
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
Product 1
Reagents, catalysts & solvents 1
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
- customat room temperature
- customfor 4 hours
- filtrationThe reaction mixture was filtered
- concentrationconcentrated
- customabsorbed on to an SCX column (3×50 g), which
- washwas then washed with methanol
- washeluted with ammonia in methanol
- additionConcentration of product containing fractions
Sources & evidence
- ORD record
- ord-7291eb837dae4ec89eec34d474cecb2e
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709471B2
Reaction notes
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