Sodium Methoxide → 6-(4-Butoxyphenyl)-4-hydroxy-6-methyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile

HRID 1629801Notes

Reaction equation

HRID 1629801 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([NH:19][C:20](=[O:24])[CH2:21][C:22]#[N:23])([CH3:18])[CH2:13][C:14]([O:16]C)=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C[O-].[Na+]>CO>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2([CH3:18])[NH:19][C:20](=[O:24])[C:21]([C:22]#[N:23])=[C:14]([OH:16])[CH2:13]2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86685894Methyl 3-(4-butoxyphenyl)-3-(2-cyanoacetamido)butanoate

Product 1

HCID 866858956-(4-Butoxyphenyl)-4-hydroxy-6-methyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrileYield 102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
55 °C

Procedure

To a stirred solution of Intermediate 107D (218 mg, 0.656 mmol) in MeOH (5 mL) was added 4.37 M NaOMe (0.750 mL, 3.28 mmol) in methanol solution. The reaction was heated to 55° C. for 5 h. The reaction mixture was concentrated and the residue was diluted with EtOAc. The organic layer was washed with 1 M HCl, dried over MgSO4, filtered and concentrated to yield the desired product (200 mg, 102%) as a light yellow solid. LCMS Anal. Calc'd for C17H20N2O3 300.15, found [M+H] 301.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with EtOAc
  3. washThe organic layer was washed with 1 M HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5e778c26e1034b51a38140affa11e5fc
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

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