1-Adamantanecarbonyl chloride → HCID 10447478, compound

HRID 234646Notes

Reaction equation

HRID 234646 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:10])([CH3:9])[CH3:8])=[CH:3][CH:2]=1.C([Li])CCC.[C:16]12([C:26](Cl)=[O:27])[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2>C1COCC1.CCCCCC>[C:16]12([C:26]([O:10][C:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)([CH3:9])[CH3:8])=[O:27])[CH2:23][CH:22]3[CH2:21][CH:20]([CH2:19][CH:18]([CH2:24]3)[CH2:17]1)[CH2:25]2

Participants

6

Reactant 3

HCID 989151-Adamantanecarbonyl chlorideHCID 45805832-(4-Pyridyl)-2-propanolHCID 178418339Butyllithium

Product 1

HCID 10447478HCID 10447478, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

The method followed that described in Example 1, but using 2-(4-pyridyl)propan-2-ol (0.69 g, 5.0 mmol) in THF (20 ml), n-butyllithium (2.5 M; 2.0 ml, 5.0 mmol) in hexane, and 1-adamantanecarbonyl chloride (1.09 g, 5.5 mmol) in THF (6 ml). Chromatography, on elution with ether-petrol-triethylamine 50:50:1, gave the title compound (1.06 g, 71%) as an oil. IR νmax 1730 cm-1 ; 1H-NMR (CDCl3) δ1.71 (6H, s, CMe2), 1.71 and 1.90 (12H, 2s, adamantyl CH2), 2.02 (3H, s, adamantyl CH), 7.23 (2H, d, J 6.1 Hz, Py 3 and 5-H), 8.56 (2H, d, J 6.1 Hz, Py 2 and 6-H). Anal. Calcd: C, 76.22; H, 8.42; N, 4.68. Found: C, 76.17; H, 8.47; N, 4.64%.

Workup

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

Sources & evidence

ORD record
ord-a7d660b7ee7245e98bc2a2c8d7482b91
Source dataset
uspto-grants-1997_01
Patent number
US05595995

Reaction notes

Loading…