Diisopropylcarbodiimide → Methyl 3-(pyridin-3-yl)propanoate
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH:2]=1.[CH:12](N=C=NC(C)C)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CO.CN(C1C=CN=CC=1)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:2]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 23 °C
Procedure
To a solution of 3-(3-pyridinyl)propanoic acid (2.50 g, 16.5 mmol) in CH2Cl2 (110 mL) and MeOH (1 mL) was added DMAP (0.010 g, 0.082 mmol) and diisopropylcarbodiimide (4.17 g, 33.1 mmol). The reaction was stirred for 2 hours at 23° C. then saturated aqueous NaHCO3 (100 mL) was added. The mixture was extracted with CH2Cl2 (100 mL) and the combined extracts were dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (elution with 60% EtOAc/hexanes) to provide 2.70 g (99%) of the desired product. MS (DCI/NH3) m/z 166 (M+H)30 .
Workup
- extractionThe mixture was extracted with CH2Cl2 (100 mL)
- dry with materialthe combined extracts were dried over Na2SO4
- filtrationfiltered
- customevaporated in vacuo
- customThe residue was purified by flash chromatography on silica gel (elution with 60% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-326ce4ce0447409aa6498b04284cbdc6
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06495576B2
Reaction notes
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