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

HRID 324831Notes

Reaction equation

HRID 324831 reaction equation
[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:7]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:6]([CH:24]([CH3:26])[CH3:25])[N:5]=1)([CH3:3])[CH3:2].[CH2:27]([Li])[CH2:28][CH2:29][CH3:30]>C(Cl)Cl.CCCCCC>[CH:1]([C:4]1[C:9]([CH:10]([OH:11])[CH2:27][CH2:28][CH2:29][CH3:30])=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[C:7]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:6]([CH:24]([CH3:25])[CH3:26])[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 220049552,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-pentylpyridineHCID 178418339Butyllithium

Product 1

HCID 22005001(+/-)-2,6-Diisopropyl-3-(1-hydroxypentyl)-4-(4-fluorophenyl)-5pentyl-pyridine

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Procedure

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).

Sources & evidence

ORD record
ord-ce92016d612b40c58f5423089e256c77
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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