S)-1-(5-fluoropyridin-2-yl)ethanaMine synthesis

9synthesis methods

Product Name:S)-1-(5-fluoropyridin-2-yl)ethanaMine
CAS Number:905587-15-7
Molecular formula:C7H9FN2
Molecular Weight:140.16

(S)-tert-butyl 1-(5-fluoropyridin-2-yl)ethylcarbaMate

905587-16-8
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905587-15-7
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Yield:905587-15-7 98%

Reaction Conditions:

Stage #1: (S)-tert-butyl-1-(5-fluoropyridin-2-yl)ethylcarbamatewith hydrogenchloride in 1,4-dioxane;dichloromethane at 20; for 3 h;
Stage #2: with sodium hydrogencarbonate in water;

Steps:

33

To the solution of (5)-tert-butyl-l-(5-fluoropyridin-2-yl)ethylcarbamate (Method 34, 12.8 g, 53.3 mmol) in DCM (100 ml) was added HCl/dioxane solution (107 ml, 4 N, 428 mmol). The reaction was stirred at room temperature for 3 hours. The solvent was removed and 50 ml of saturated sodium bicarbonate was added. The resulting aqueous solution was extracted with ether (6 x 400 ml), dried over sodium sulfate and concentrated to give the title compound (7.30 g, 98%) as pale yellow oil. ¹H NMR (400 MHz) δ 8.44 (d, J= 2.8 Hz, IH), 7.66 (m, IH), 7.53 (m, IH), 4.01 (q, J= 6.8 Hz, IH), 1.94 (b, 2H), 1.26 (d, J= 6.8 Hz, 3H). MS: Calcd.: 140; Found: [M+H]⁺ 141.

References:

WO2006/82392,2006,A1 Location in patent:Page/Page column 104