Triethylamine → Methyl 1-(aminomethyl)cyclopentanecarboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:10][NH:11]C2CCCC2)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].ClC1N=C(Cl)C([N+]([O-])=O)=CN=1.C(N(CC)CC)C>C(#N)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
5
Procedure
Methyl1-[(cyclopentylamino)methyl]cyclopentane-1-carboxylate (Intermediate 258; 1.60 g, 7.10 mmol), 2,4-dichloro-5-nitropyrimidine (Aldrich; 1.66 g, 8.52 mmol) and triethylamine (1.2 mL, 8.52 mmol) were stirred in acetonitrile (50 mL) for 4 hours. The reaction mixture was evaporated and the residue dissolved in DCM, washed with water, dried (MgSO4) and evaporated. The residue was purified on a silica column eluting with 1% methanol/DCM to yield the title compound as a yellow oil that crystallised on standing (945 mg, 35%).
Workup
- customThe reaction mixture was evaporated
- dissolutionthe residue dissolved in DCM
- washwashed with water
- dry with materialdried (MgSO4)
- customevaporated
- customThe residue was purified on a silica column
- washeluting with 1% methanol/DCM
Sources & evidence
- ORD record
- ord-d8121f9908d746bda69347704d412b5f
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709471B2
Reaction notes
Loading…