HCID 67483427, compound → HCID 135819145, compound

HRID 324867Notes

Reaction equation

HRID 324867 reaction equation
[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18]CC3C=CC=CC=3)=[CH:14][CH:13]=2)[C:7]([CH:26]=[CH:27][CH2:28][CH2:29][CH3:30])=[C:6]([CH:31]([CH3:33])[CH3:32])[N:5]=1)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)[C:7]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[C:6]([CH:31]([CH3:32])[CH3:33])[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67483427HCID 67483427, compound

Product 1

HCID 135819145HCID 135819145, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,6-Diisopropyl-3-hydroxymethyl-4-(4benzyloxyphenyl)-5-(pent-1-enyl)pyridine (Example 160) (500 mg, 1.13 mmol) was dissolved in absolute ethanol (10 mL) under argon, treated with 10% palladium on carbon (15 mg), then stirred under a hydrogen atmosphere for 14 h. After purging the system with argon, the catalyst was removed by filtration through a pad of Celite. The solvent was removed and the residue purified by flash chromatography (5% methanol-methylene chloride) to yield 371 mg of the title compound as a waxy solid (mp 158.5° C.). 1H NMR (300 MHz, CDCl3): δ 0.79 (t, J=6.6 Hz, 3 H), 1.06-1.36 (m, 21 H), 2.24-2.31 (m, 2 H), 3.22 (sept, J=6.6 Hz, 1 H), 3.40 (sept, J=6.6 Hz, 1 H), 4.36 (d, J=5.4 Hz, 2 H), 4.85 (s, 1 H), 6.89 (d, J=8.4 Hz, 1 H), 7.05 (d, J=8.7 Hz, 1 H).

Workup

  1. customAfter purging the system with argon
  2. customthe catalyst was removed by filtration through a pad of Celite
  3. customThe solvent was removed
  4. customthe residue purified by flash chromatography (5% methanol-methylene chloride)

Sources & evidence

ORD record
ord-479108ecfe3a4cb98c581a134b8cbf08
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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