Erreaktibo organolitikoak sintesi asimetrikoan, aminen ...
Erreaktibo organolitikoak sintesi asimetrikoan, aminen ...
Erreaktibo organolitikoak sintesi asimetrikoan, aminen ...
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S. Arrasate Doktorego-Tesia<br />
es: %66 (Chiralcel OD, hexano/2-propanol %4, 1 mL/min, tr (R) = 24.8 min (%83.1); tr<br />
(R) = 26.7 min (%16.9).<br />
1 H-NMR (δ, ppm): 1.18 (d, J = 6.3 Hz, 3H, CH3), 2.71 (dd, J = 9.2, 13 Hz, 1H,<br />
CHaHbCHN), 3.14 (dd, J = 6.6, 13 Hz, 1H, CHaHbCHN), 3.61-3.68 (m, 1H, CH2CHN),<br />
3.76 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 3.85 (s, 3H, OCH3). 6.65-6.84 (m, 7H, Harom).<br />
13 C-NMR (δ, ppm): 20.3 (CH3), 41.7 (CH2CHCH3N), 50.4 (CH2CHCH3N), 55.8, 55.9<br />
(3 × OCH3), 111.1, 112.8 (C2’, C5’ ), 114.9 (C2, C6), 115.2 (C3, C5), 121.5 (C6’), 131.0<br />
(C1’), 141.3 (C1), 147.5, 148.7 (C4’, C3’), 152.1 (C4).<br />
IR (CHCl3): 3406 (N-H), 1510 (C=C), 1261 (C-N) cm -1 .<br />
E.M. (IE) [m/z (ugaritasun erlatiboa)]: 301 (M + , 2), 302 (M +1 , 1), 151 (14), 150 (100),<br />
135 (5), 119 (3), 108 (4), 77 (4).<br />
5.3. FENETILAMINEN SINTESI ENANTIOSELEKTIBOA.<br />
5.3.1. Aitzindarien <strong>sintesi</strong>a.<br />
5.3.1.1. 15 N-(2,2-dimetilpropiliden)-p-anisidinaren <strong>sintesi</strong>a.<br />
Dietil eterretan dagoen p-anisidinaren (1.23 g, 10 mmol) disoluzioari,<br />
trimetilazetaldehidoa (0.98 mL, 9.1 mmol) gehitu zitzaion bahe molekularraren<br />
presentzian. Erreakzio-nahastea birfluxuan mantendu zen 16 orduz. Adierazitako<br />
denbora iragan ondoren, iragazi zen eta disolbatzailea hutsean lurrundu zen, 15 imina<br />
(1.82 mg, 9.5 mmol), n-pentanotan kristaldu zuen solido marroi bezala lortu zelarik.<br />
180<br />
CH C(CH3) 3<br />
N<br />
OCH 3<br />
Etekina: %95.<br />
U.p.: 51-53 o C (n-pentanotan).<br />
Bib. 6 50-52 o C.