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

HRID 324823Notes

Reaction equation

HRID 324823 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.[CH2:27]([Mg]Br)[CH3:28]>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:3])[CH2:27][CH3:28])=[C:11]([CH:12]([CH3:13])[CH3:14])[N:10]=1)([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 22005047Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-formyl-pyridine-5-carboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 22004986(+/-)-2,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-(1-hydroxy-propyl)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 ethyl magnesium bromide, according to the procedures described in Example 93. 1H NMR (300 MHz, CDCl3): δ 7.15 (m, 4 H), 4.40 (dq, J=3.7, J=5.2 Hz, 1 H), 4.30 (d, 5.5 Hz, 2 H), 3.72 (septet, J=6.6 Hz, 1 H), 3.42 (septet, 6.6 Hz, 1 H), 1.88 (m, 1 H), 1.63 (t, J=5.5 Hz, 1 H), 1.27 (m, 14 H), 0.804 (t, J=7.36 Hz, 3 H). FAB-MS: calcd for (C21H28NFO2) 345, found 346 (M+H). Anal. Calcd for C21H28NO2F: C, 76.84; H, 8.69; N, 3.90. Found: C, 76.67; H, 8.76; N, 3.77. mp 173-175° C. Rf=0.2 (20% ethyl acetate/hexane);

Sources & evidence

ORD record
ord-675b0ee8535442f7b59a5eac32e01103
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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