L-Proline → Methyl 5-(1,8-naphthyridin-2-yl)pentanoate

HRID 379212Notes

Reaction equation

HRID 379212 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8](=O)[CH3:9].[NH2:12][C:13]1[C:18]([CH:19]=O)=[CH:17][CH:16]=[CH:15][N:14]=1.N1CCC[C@H]1C(O)=O>C(O)C>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:19][C:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 288022Heptanoic acid, 6-oxo-, methyl esterHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 11447926Methyl 5-(1,8-naphthyridin-2-yl)pentanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-2 (1.4 g, 9.04 mmol), 1-3, 2-amino-3-formylpyridine (552 mg, 4.52 mmol) (for preparation, see: J. Org. Chem., 1983, 48, 3401), and proline (260 mg, 2.26 mmol) in absolute ethanol (23 mL) was heated at reflux for 18 h. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 80% ethyl acetate/hexane, then ethyl acetate) to give ester 1-4 as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. customremoval of the solvent
  4. customthe residue was chromatographed (silica gel, 80% ethyl acetate/hexane

Sources & evidence

ORD record
ord-be2027ac6d3544148f5ababba2cca3d5
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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