Pyridine, 3-(2R)-oxiranyl- (9CI) synthesis

5synthesis methods

Product Name:Pyridine, 3-(2R)-oxiranyl- (9CI)
CAS Number:174060-40-3
Molecular formula:C7H7NO
Molecular Weight:121.14

173901-03-6 Synthesis

173901-03-6
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174060-40-3
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Yield:174060-40-3 94%

Reaction Conditions:

with potassium carbonate in acetonitrile; for 2.5 h;Heating / reflux;

Steps:

2 (R)-(Pyridin-3-yl)oxirane

To a solution of (R)-2-chloro-1-pyridin-3-ylethanol (2.0 g, 12.7 mmol) in acetonitrile (100 ml) is added potassium carbonate (7.02 g). The mixture is refluxed for 2.5 hours, and cooled to room temperature. The mixture is filtered, and the filtrate is distilled off under reduced pressure. The resultant is purified by silica gel column chromatography (methanol/chloroform = 1/100) to give the title compound (R)-(pyridin-3-yl)oxirane (1.46 g, yield: 94 %) as pale yellow oil. 1H-NMR (CDCl3) δ: 2.83 (1H, dd, J=2.5, 5.3Hz), 3.21 (1H, dd, J=4.1, 5.3Hz), 3.90 (1H, dd, J=2.6, 4.0Hz), 7.29 (1H, dd, J=5.1, 8.3Hz), 7.53-7.56 (1H, m), 8.57 (1H, dd, J=1.6, 4.8Hz), 8.60 (1H, d, J=2.0Hz).

References:

EP1514869,2005,A1 Location in patent:Page/Page column 20

500-22-1 Synthesis