Lithium Hydroxide → HCID 61727402, compound

HRID 253126Notes

Reaction equation

HRID 253126 reaction equation
[CH:1]1([N:7]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]([C:14]([O:16]C)=[O:15])=[CH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1.CO>[CH:1]1([N:7]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]([C:14]([OH:16])=[O:15])=[CH:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 15946190Methyl 1-cyclohexyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 61727402HCID 61727402, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 1-cyclohexyl-6-oxo-1,6-dihydropyridine-3-carboxylate (100 mg, 0.43 mmol) in 10 mL of THF:MeOH (3:1) was added 1M LiOH (1 mL, 1 mmol). The solution was stirred at room temperature until starting material was consumed as determined by LC-MS. The solution was then concentrated in vacuo, acidified with 2 N HCl to pH 2, and extracted with EtOAc (3×). The combined EtOAc layers were washed with brine, dried over MgSO4, and concentrated in vacuo to give 60 mg (63%) of the title compound as a golden yellow solid. MS m/z: 222.1(M+1).

Workup

  1. customwas consumed
  2. concentrationThe solution was then concentrated in vacuo
  3. extractionextracted with EtOAc (3×)
  4. washThe combined EtOAc layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7b4bc6abe6a479b861bf0a4f7ea38e8
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

Loading…