Reaktion #411978

Reaktionsgleichung

intermediate

2,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-(1-pentenyl)pyridine

→

title compound

Ausbeute 98.0%

2,6Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-pentylpyridine

Ausbeute 98.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter purging the system with argon
2. 2
   Sonstigethe catalyst was removed by filtration through a pad of Celite
3. 3
   SonstigeThe solvent was removed
4. 4
   Sonstigethe product dried in vacuo

Vorschrift

The intermediate obtained in Step G was dissolved in absolute ethanol (50 mL) under argon, treated with 10% palladium on carbon (140 mg, 0.1 eq), then stirred under a hydrogen atmosphere for 2 hr. After purging the system with argon, the catalyst was removed by filtration through a pad of Celite. The solvent was removed and the product dried in vacuo to afford the title compound as a white solid (1.4 g, 3.9 mmol, 98%). 1H NMR (300 MHz, CDCl3 ): δ7.15 (m, 4 H), 4.33 (d, J=4.4 Hz, 2 H), 3.41 (sept, J=6.6 Hz, 1 H), 3.23 (sept, J =6.6 Hz, 1 H), 2.26 (m, 2 H), 1.33 (d, J=6.6 Hz, 6 H), 1.30 (d, J=6.6 Hz, 6 H), 1.27 (m, 2 H), 1.13 (m, 5 H), 0.79 (t, J=6.6 Hz, 3 H). FAB-MS: calculated for (C23H32FNO) 357, found 358 (M+H). Anal. calcd for C23H32FNO: C, 77.27; H, 9.02; N, 3.92. Found: C, 77.46; H, 8.95; N, 3.78. Rf=0.3 (20% ethyl acetate/hexane). mp 100-101° C.

Quelle