Triethylamine → Methyl trans-2-{[(cyanomethyl)amino]carbonyl}cyclopentanecarboxylate
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10]([OH:12])=O)=[O:4].Cl.[NH2:14][CH2:15][C:16]#[N:17].F[P-](F)(F)(F)(F)F.N1([PH+](N2CCCC2)N2CCCC2)CCCC1.C(N(CC)CC)C>CN(C)C=O>[C:15]([CH2:16][NH:17][C:10]([C@@H:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:3]([O:2][CH3:1])=[O:4])=[O:12])#[N:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Cyclopentane-1,2-dicarboxylic acid monomethyl ester (2.21 g, 12.8 mmol), 2-aminoacetonitrile hydrochloride (1.48 g, 16.0 mmol) and benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) (7.34 g, 14.1 mmol) were dissolved in dimethylformamide (26 mL) and the reaction mixture was cooled to 0° C. Triethylamine (4.9 mL, 35 mmol) was added and the reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was partitioned between water (150 mL) and ethyl acetate (100 mL). The product was extracted into ethyl acetate, washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on silica gel with 3:2 ethyl acetate:hexanes eluent to give methyl trans-2-{[(cyanomethyl)amino]carbonyl}cyclopentanecarboxylate as a colorless solid.
Workup
- customThe reaction mixture was partitioned between water (150 mL) and ethyl acetate (100 mL)
- extractionThe product was extracted into ethyl acetate
- washwashed with saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe residue was chromatographed on silica gel with 3:2 ethyl acetate
Sources & evidence
- ORD record
- ord-00527ddaf1df475ca700b359b698bed5
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07371747B2
Reaction notes
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