ChemicalBook CAS DataBase List (R)-1-(Pyrid-3-yl)-2-chloroethanol

(R)-1-(Pyrid-3-yl)-2-chloroethanol synthesis

4synthesis methods

Product Name:(R)-1-(Pyrid-3-yl)-2-chloroethanol
CAS Number:173901-03-6
Molecular formula:C7H8ClNO
Molecular Weight:157.6

61889-48-3 Synthesis

3-(2-Chloroacetyl)pyridine hydrochloride

61889-48-3
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173901-03-6
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Yield:173901-03-6 82%

Reaction Conditions:

with triethylamine;(-)-diisopinocamphenylborane chloride in tetrahydrofuran at -25; for 72 h;

Steps:

1 (R)-2-Chloro-1-pyridin-3-ylethanol

To a solution of (-)-B-chlorodiisopinocampheylborane [(-)-DIP-Cl] (25 g, 77.9 mmol) in tetrahydrofuran (90 ml) are added with stirring 3-(2-chloroacetyl)pyridine hydrochloride (Can. J. Chem., vol. 61, p. 334 (1983)) (3.0 g, 15.6 mmol) and triethylamine (2.39 ml, 17.2 mmol) at -25°C, and the reaction mixture is stirred at -25°C for 3 days. To this mixture is added water (300 ml), and the mixture is warmed to room temperature. To the mixture is added ethyl acetate, and the organic phase is separated. The aqueous phase is neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted 6 times with ethyl acetate. The combined organic phase is dried over sodium sulfate, and concentrated under reduced pressure to give yellow oil, which is purified by silica gel column chromatography (methanol/chloroform = 1/20) to give the title compound (R)-2-chloro-1-pyridin-3-ylethanol (2.02 g, yield: 82 %) as pale yellow oil. 1H-NMR (CDCl3) δ: 2.75 (1H, d, J=3.4Hz), 3.67 (1H, dd, J=8.5, 11.3Hz), 3.78 (1H, dd, J=3.5, 11.3Hz),, 4.96-5.00 (1H,m), 7.33 (1H, dd, J=4.9, 7.9Hz), 7.75-7.78 (1H, m), 8.59 (1H, dd, J=1.6, 4.8Hz), 8.64 (1H, d, J=2.2Hz).

References:

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

55484-11-2 Synthesis