Erreaktibo organolitikoak sintesi asimetrikoan, aminen ...

S. Arrasate Doktorego-Tesia
organiko batuak Na2SO4 anhidroz lehortu, iragazi eta disolbatzailea hutsean
kontzentratu zen. Flash zutabe-kromatografiaren bidez purifikatu ondoren (silize-gela,
hexano/AcOEt %30) 3d N-[(1-butil)-bentzil]-p-toluensulfonamida (54 mg, 0.16 mmol),
hexanotan kristaltzen den solido zuri bezala lortu zen.
Bu
NH SO2 CH3
Etekina: %62.
U.p.: 74-76 o C (hexano).
es: %0 (Chiralcel OD, hexano/2-propanol %3, 0.7 mL/min, tr (S) = 18.5 min (%49.9); tr
(R) = 28.9 min (%50.1).
1 H-NMR (δ, ppm): 0.78 (t, J = 6.7 Hz, 3H, CH2CH2CH2CH3), 1.21-1.25 (m, 4H,
CH2CH2CH2CH3), 1.69-1.72 (m, 2H, CH2CH2CH2CH3), 2.34 (s, 3H, SO2PhCH3), 4.24
(dt, J = 7.14, 14.67 Hz, 1H, CHNH), 5.37 (d, J = 7.1 Hz, 1H, NH), 7.01-7.11 (m, 7H,
Harom), 7.53 (d, J = 7.9 Hz, 2H, H2, H6).
13 C-NMR (δ, ppm): 13.8 (CH2CH2CH2CH3) 21.4 (CH3), 22.1 (CH2CH2CH2CH3), 27.9
(CH2CH2CH2CH3), 37.3 (CH2CH2CH2CH3), 58.3 (CHNH), 126.4, 127.0, 127.1, 128.3,
129.2 (9 × Carom-H), 137.6 (C1), 141.0 (C1’), 142.8 (CaromCH3).
IR (CH2Cl2): 3269 (NH), 2919 (C-H), 1595 (NH), 1454 (CH3) 1155 (SO2) cm -1 .
E.M. (IE) [m/z (ugaritasun erlatiboa)]: 262 (9), 261 (11), 261 (21), 260 (100), 155 (45),
104 (11), 91 (60), 65 (12).
Analisi elementala: C18H23NO2S
172
Kalkulatua: %C: 68.10 %H: 7.30 %N: 4.41.
Lortutakoa: %C: 68.17 %H: 7.83 %N: 3.91.