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

HRID 324825Notes

Reaction equation

HRID 324825 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])([O:3]CC)=O.[C:27]1([Li])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(OCC)(=O)C.CCCCCC>[CH:15]([C:9]1[C:8]([CH2:18][OH:19])=[C:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:6]([CH:1]([OH:3])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[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 178506676HCID 178506676, compound

Product 1

HCID 22005067(+/-)-2,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-(hydroxy-phenylmethyl)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 phenyllithium, according to the procedures described in Example 93. 1H NMR (300 MHz, CDCl3): δ 7.23 (m, 7 H), 7.06 (m, 2 H), 5.71 (d, J=5.14 Hz, 1 H), 4.38 (d, J=5.5 Hz, 2 H), 3.47 (septet, J=6.6 Hz, 1 H), 3.12 (septet, J=6.6 Hz, 1 H), 2.12 (d, J=5.1 Hz, 1 H), 1.57 (s, 1H), 1.29 (m, 10 H), 0.797 (d, J=6.6 Hz, 3 H). FAB-MS: calcd for (C25H28NFO2) 393, found 394 (M+H). Anal. Calcd for C25H28NO2F: C, 76.84; H, 8.69; N, 3.90. Found: C, 76.67; H, 8.76; N, 3.77. mp 202-204° C. Rf=0.2 (20% ethyl acetate/hexane).

Sources & evidence

ORD record
ord-bbf3a8e853b34bd3b82cec85e556f5ef
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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