Methanol → Methyl 1-cyclohexyl-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 253125Notes

Reaction equation

HRID 253125 reaction equation
O=[C:2]1[O:7][CH:6]=[C:5]([C:8]([O-:10])=[O:9])[CH:4]=[CH:3]1.[CH:11]1([NH2:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[CH3:18]O>>[CH:11]1([N:17]2[C:2](=[O:7])[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:18])=[O:9])=[CH:6]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 887MethanolHCID 7965CyclohexylamineHCID 6931293HCID 6931293, compound

Product 1

HCID 15946190Methyl 1-cyclohexyl-6-oxo-1,6-dihydropyridine-3-carboxylateYield 26%

Procedure

To a solution of 6-oxo-6H-pyran-3-carboxylate (1.14 g, 7.4 mmol, Aldrich) and 20 mL of MeOH was added cyclohexylamine (2.50 mL, 21.9 mmol, Aldrich). The solution was stirred at reflux for 16 hours, then concentrated in vacuo. The crude material was chromatographed through a Redi-Sep® pre-packed silica gel column (12 g), eluting with 5% to 20% EtOAc:hexane to give 460 mg (26%) of the title compound as a dark yellow oil. MS m/z: 236.4(M+1).

Workup

  1. temperatureat reflux for 16 hours
  2. concentrationconcentrated in vacuo
  3. customThe crude material was chromatographed through a Redi-Sep® pre-packed silica gel column (12 g)
  4. washeluting with 5% to 20% EtOAc

Sources & evidence

ORD record
ord-28eff0fe42a740b2a2ac55ad2430bb25
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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