Lithium Carbonate → HCID 22620209, compound

HRID 1919707Notes

Reaction equation

HRID 1919707 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:13]([CH3:14])=[CH:12][C:11](Cl)=[CH:10][CH:9]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]C)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Li+].[Li+].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:13]([CH3:14])=[CH:12][CH2:11][CH2:10][CH:9]1[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11125Lithium CarbonateHCID 22620204HCID 22620204, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22620209HCID 22620209, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 1-(tert-Butoxycarbonyl)-4-chloro-6-methyl-2-n-hexyl-1,2-dihydropyridine (3.74 g, 11.91 mmol) in 250 mL of MeOH at 0° C. was added of lithium carbonate (0.88 g, 11.91 mmol) followed by 5% Pd/C. The mixture was placed under a positive pressure of hydrogen gas from a balloon, and the reaction progress was monitored by removing aliquots with a syringe, concentrating the aliquot in vacuo, and examining its 1H NMR spectrum. Upon completion, the mixture was filtered through Celite and evaporated. The residue was dissolved in ether (100 mL) and water (50 mL) was added, and the aqueous phase was extracted twice with ether. The combined organic extracts were washed with 1M NaOH and brine. The organic phase was dried with potassium carbonate, filtered through Celite, and concentrated in vacuo to give the crude product. Purification by column chromatography (silica gel, 5% EtOAc in hexanes) afforded 2.09 g (62%) as a clear oil that was homogeneous by TLC analysis. 1H NMR (300 MHz) δ 4.85 (br s, 1H), 4.43-4.38 (m, 1H), 2.01 (s, 3H), 1.99-1.91 (m, 2H), 1.83-1.12 (m, 23H), 0.89-0.84 (t, 3H).

Workup

  1. customby removing aliquots with a syringe
  2. concentrationconcentrating the aliquot in vacuo
  3. filtrationUpon completion, the mixture was filtered through Celite
  4. customevaporated
  5. dissolutionThe residue was dissolved in ether (100 mL)
  6. additionwater (50 mL) was added
  7. extractionthe aqueous phase was extracted twice with ether
  8. washThe combined organic extracts were washed with 1M NaOH and brine
  9. dry with materialThe organic phase was dried with potassium carbonate
  10. filtrationfiltered through Celite
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-263c4c23758c45aea74c59b5a3d7ea2c
Source dataset
uspto-grants-2012_05
Patent number
US08168657B2

Reaction notes

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