2,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-pentylpyridine → (+/-)-2,6-Diisopropyl-3-(1-hydroxypentyl)-4-(4-fluorophenyl)-5pentyl-pyridine

Participants

Reaction Steps

The title compound was prepared from 2,6-diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-pentylpyridine (Example 1) and butyllithium according to the procedures described in Example 114. 1H NMR (300 MHz, CDCl3): δ 6.95 (m, 4 H), 4.33 (m, 1 H), 3.59 (septet, J=6.6 Hz, 1 H), 3.09 (septet, J=6.6 Hz, 1 H), 2.08 (t, J=5.2 Hz, 2 H), 1.75 (m, 2 H), 1.47 (m, 2 H), 1.04 (m, 22 H), 0.719 (t, J=7.0 Hz, 3 H), 0.674 (t, J=7.0 Hz, 3 H). FAB-MS: calcd for (C27H40FNO) 413, found 414 (M+H). Anal. Calcd for C27H40FNO: C, 78.41; H, 9.75; N, 3.39; F, 4.59. Found: C, 77.84; H, 9.51; N, 3.27; F. 5.08. mp 66-68° C. Rf=0.2 (50% CH2Cl2/hexane).

Provenance & Evidence