HCID 67483427, compound → HCID 135819145, compound

Participants

Reaction Steps

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).

Provenance & Evidence