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

HRID 1696308Notes

Reaction equation

HRID 1696308 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-ac954ef7d2cf4bdab733573a6f87e3e2
Source dataset
uspto-grants-2012_04
Patent number
US08163766B2

Reaction notes

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