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

HRID 324824Notes

Reaction equation

HRID 324824 reaction equation
[C:1]([C:6]1[C:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:8]([CH:18]=[O:19])[C:9]([CH:15]([CH3:17])[CH3:16])=[N:10][C:11]=1[CH:12]([CH3:14])[CH3:13])(OCC)=[O:2].[CH2:27]([Li])[CH2:28][CH2:29][CH3:30]>C(OCC)(=O)C.CCCCCC>[CH:15]([C:9]1[C:8]([CH2:18][OH:19])=[C:7]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[C:6]([CH:1]([OH:2])[CH2:27][CH2:28][CH2:29][CH3:30])=[C:11]([CH:12]([CH3:13])[CH3:14])[N:10]=1)([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 22005047Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-formyl-pyridine-5-carboxylateHCID 178418339Butyllithium

Product 1

HCID 22004992(+/-)-2,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-(1-hydroxy-pentyl)pyridine

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

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).

Sources & evidence

ORD record
ord-2301537ea6c14e8f98b8fbc74ffea1d2
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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