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Helvetica Chimica Acta – Vol. 96 (2013)
hour and then extracted with CH2Cl2 (3 ꢁ 10 ml). The extract was dried (Na2SO4) and concenterated: 7
(99%). Light yellow semi-solid. 1H-NMR (500 MHz, CDCl3): 1.85 – 1.95 (m, 1 H); 2.30 – 2.44 (m, 1 H);
2.40 – 252 (m, 1 H); 2.68 – 2.80 (m, 2 H); 2.96 – 3.04 (m, 1 H); 3.60 (dd, J ¼ 11.4, 10.2, 2 H); 4.28 – 4.34 (m,
1 H); 6.60 – 6.70 (m, 2 H); 7.00 (d, J ¼ 8.4, 1 H); 7.10 (t, J ¼ 7.0, 1 H). 13C-NMR (125 MHz, CDCl3): 37.0;
54.5; 54.1; 65.6; 73.4; 115.6; 117.8; 123.5; 128.3; 129.8; 146.4. HR-ESI-MS: 211.1008 (Mþ, C11H16ClN2þ ;
calc. 211.1002).
2-(Pyrrolidin-1-ylmethyl)benzenamine (9). As described for 7; with 3-deoxyvasicine (8; 0.5 g,
2.9 mmol; prepared as described in [31]), MeOH/H2O 1:1 (10 ml), and NaBH4 (0.35 g , 10 mmol); 9
(99%). Light yellow semi-solid. 1H-NMR (400 MHz, CDCl3): 1.64 – 1.72 (m, 2 H); 1.73 – 1.78 (m, 2 H);
3.11 (t, J ¼ 6.4, 2 H); 3.46 (t, J ¼ 6.9, 2 H); 3.67 (s, 2 H); 6.61 – 1.69 (m, 2 H); 7.15 – 7.25 (m, 2 H).
13C-NMR (100 MHz, CDCl3): 36.8; 38.2; 52.1; 58.9; 62.1; 115.8; 117.6; 123.4; 128.4; 129.8; 146.3. HR-ESI-
MS: 177.1396 (Mþ, C11H17Nþ2 ; calc. 177.1392).
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