Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-formyl-pyridine-5-carboxylate → (+/-)-2,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-(1-hydroxy-pentyl)pyridine

Participants

Reaction Steps

The title compound was prepared from 5-carboethoxy-2,6-diisopropyl-4-(4-fluorophenyl)-3-pyridinecarboxaldehyde (Example 1, Step E) and n-butyllithium, according to the procedures described in Example 93. 1H NMR (300 MHz, CDCl3): δ 7.16 (m, 4 H), 4.49 (m, 1 H), 4.31 (d, J=5.5 Hz, 2 H), 3.74 (septet, J=6.6 Hz, 1 H), 3.42 (septet, J=6.6 Hz, 1 H), 1.88 (m, 1 H), 1.58 (d, J=3.3 Hz, 1 H), 1.18 (m, 18 H), 0.821 (t, J=4.1 Hz, 3 H). FAB-MS: calcd for (C23H32NFO2) 373, found 374 (M+H). Anal. Calcd for C23H32NO2F: C, 73.96; H, 8.64; N, 3.75; F, 5.09. Found: C, 73.81; H, 8.60; N, 3.58; F, 5.02. mp 166-168° C. Rf=0.3 (20% ethyl acetate/hexane).

Provenance & Evidence