Erreaktibo organolitikoak sintesi asimetrikoan, aminen ...

5. Kapitulua Atal Esperimentala
Hondakina zutabe-kromatografiaz (silize-gela, AcOEt) purifikatu ondoren, n-pentanotan
kristaltzen duen 47a isokinolina (27 mg, 0.09 mmol) lortu zen solido horixka modura.
H3CO
H3CO
H 3C
N
OH
O
Etekina: %36.
[α]D 20 : -203 º (c = 0.046, CH2Cl2).
U.p.: 124-126 o C (n-pentano).
es: %99 (Chiralcel OJ, hexano/2-propanol %10, 1 mL/min, tr (S) = 32.3 min (%100).
1 H-NMR (δ, ppm): 1.55 (s, 3H, CH3-C10b), 2.05-2.19 (m, 1H, H1a), 2.31-2.47 (m, 2H, 2
× H2), 2.59 (dd, J = 16.2, 3.6 Hz, 1H, H6ec), 2.59-2.73 (m, 1H, H1b), 3.02 (dd, J = 16.2,
11.2 Hz, 1H, H6ax), 3.55-3.67 (m, 1H, H5), 3.84 (s, 3H, CH3O), 3.86 (s, 3H, CH3O),
3.98-4.03 (m, 2H, CH2OH), 4.92 (t, J = 7.1 Hz, 1H, OH), 6.52 (s, 1H, H10), 6.69 (s,
1H,H7).
13 C-NMR (δ, ppm): 27.3 (CH3-C10b), 31.1, 31.3 (C1, C2), 34.9 (C6), 53.9 (C5), 55.8
(CH3O), 56.1 (CH3O), 62.4 (CH2-OH), 64.4 (C10b), 107.4, 112.2, (C7, C10), 124.3 (C10a),
133.9 (C6a), 147.8, 148.0 (C8, C9), 174.0 (CO).
IR (KBr): 3392 (OH), 1654 (CO) cm -1 .
E.M. (IE) [m/z (ugaritasun erlatiboa)]: 291 (M + , 8), 277 (17), 276 (100), 260 (40), 244
(11), 143 (9), 130 (10), 71 (10), 57 (15).
Analisi elementala: C16H21NO4
Kalkulatua: %C: 65.96 %H: 7.26 %N: 4.81
Lortutakoa: %C: 65.77 %H: 7.53 %N: 4.67
217