Ethyl acetate hexane → (+/-)-2,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-(1-methoxy-pentyl)pyridine
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]([CH:19]([OH:24])[CH2:20][CH2:21][CH2:22][CH3:23])=[C:6]([CH:25]([CH3:27])[CH3:26])[N:5]=1)([CH3:3])[CH3:2].[C:28](OCC)(=O)C.CCCCCC>>[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]([CH:19]([O:24][CH3:28])[CH2:20][CH2:21][CH2:22][CH3:23])=[C:6]([CH:25]([CH3:26])[CH3:27])[N:5]=1)([CH3:3])[CH3:2]Participants
3
Procedure
The title compound was prepared from (±)-2,6-diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-(1-hydroxypentyl)pyridine (Example 95) according to the procedures described in Example 98. 1H NMR (300 MHz, CDCl3): δ 7.10 (m, 4 H), 4.32 (m, 2 H), 3.92 (m, 1 H), 3.76 (septet, J=7.0 Hz, 1 H), 3.42 (septet, J=6.6 Hz, 1 H), 3.12 (s, 3 H), 1.87 (m, 1 H), 1.52 (m, 2 H), 1.19 (m, 16 H), 0.821 (t, J=7.4 Hz, 3 H). FAB-MS: calcd for (C24H34NFO2) 387, found 388 (M+H). Anal. Calcd for C24H34NO2F: C, 74.38; H, 8.84; N, 3.61; F, 4.90. Found: C, 74.38; H, 8.82; N, 3.45; F, 4.90. mp 121-123° C. Rf=0.5 (20% ethyl acetate/hexane).
Sources & evidence
- ORD record
- ord-098afe2b18884d9faa7aa205669294ab
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06218431B1
Reaction notes
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