3-Pyridinemethanol → HCID 10826001, compound

HRID 234647Notes

Reaction equation

HRID 234647 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.C([Li])CCC.[C:14]12([C:24](Cl)=[O:25])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2>C1COCC1.CCCCCC>[C:14]12([C:24]([O:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[O:25])[CH2:21][CH:20]3[CH2:19][CH:18]([CH2:17][CH:16]([CH2:22]3)[CH2:15]1)[CH2:23]2

Participants

6

Reactant 3

HCID 75103-PyridinemethanolHCID 989151-Adamantanecarbonyl chlorideHCID 178418339Butyllithium

Product 1

HCID 10826001HCID 10826001, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

The method followed that described in Example 1, but using 3-pyridylcarbinol (240 mg, 2.2 mmol) in THF (10 ml), n-butyllithium (2.5 M; 0.84 ml, 2.1 mmol) in hexane, and 1-adamantanecarbonyl chloride (397 mg, 2.0 mmol) in THF (2 ml). Chromatography, on elution with petrol-ether-triethylamine 200:50:1, gave the title compound (422 mg, 78%) as an oil. IR νmax 1728 cm-1 ; 1H-NMR (CDCl3) δ1.71 and 1.91 (12H, 2s, adamantyl CH2), 2.02 (3H, s, adamantyl CH), 5.11 (2H, s, OCH2), 7.30 (1H, m, Py 5-H), 7.66 (1H, m, Py 4-H), 8.56 (1H, m. Py 6-H), 8.61 (1H, m, Py 2-H). Anal. Calcd: C, 75.24; H, 7.80; N, 5.16. Found: C, 75.09; H, 7.84; N, 5.03%.

Workup

  1. washChromatography, on elution with petrol-ether-triethylamine 200:50:1

Sources & evidence

ORD record
ord-43141414fe2343e6be6deb9b1c840a82
Source dataset
uspto-grants-1997_01
Patent number
US05595995

Reaction notes

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