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ChemicalBook CAS DataBase List (S)-tert-Butyl (1-(5-bromopyridin-2-yl)ethyl)carbamate
915720-71-7

(S)-tert-Butyl (1-(5-bromopyridin-2-yl)ethyl)carbamate synthesis

5synthesis methods
915720-70-6 Synthesis
(S)-1-(5-Bromo-pyridin-2-yl)-ethylamine

915720-70-6
31 suppliers
$338.00/250mg

24424-99-5 Synthesis
Di-tert-butyl dicarbonate

24424-99-5
870 suppliers
$13.50/25G

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Yield:915720-71-7 68.5%

Reaction Conditions:

with triethylamine in dichloromethane at 20; for 16 h;

Steps:

Intermediate 61: (5)-tert-butyl (1 -(5-bromopyridi n-2-yl)ethyl)carbamate

Intermediate 61: (5)-tert-butyl (1 -(5-bromopyridi n-2-yl)ethyl)carbamate To a solution of (S)-1-(5-bromopyridin-2-yl)ethanamine (300 mg, 1.49 mmol) in DCM (7.5 mL)was added di-tert-butyl dicarbonate (358 mg, 1.64 mmol) and triethylamine (0.31 mL, 2.24mmol). The solution was stirred for 16 h at room temperature then washed with water andbrine. The organic layer was dried over Na2SO4, filtered and concentrated. Silica gel columnchromatography (EtOAc/heptane 0 to 80%) provided a white solid (308 mg, 68.5% yield).1H NMR (400 MHz, CDCI3) O 8.59 (d, J= 2.2 Hz, 1H), 7.76 (dd, J= 8.3, 2.4 Hz, 1H), 7.16 (d, J= 8.3 Hz, 1H), 5.57- 5.42 (m, 1H), 4.86- 4.73 (m, 1H), 1.43 (t, J= 3.4 Hz, 12H); MS m/z 303.4(M+H).

References:

WO2014/141153,2014,A1 Location in patent:Page/Page column 69; 70