Chirale Ionische Flüssigkeiten in der homogenen Katalyse

L-(-)-Prolin-methylester-chlorid 24a
Ausbeute: 98.0 % (3.9 g, 23.5 mmol)
Experimenteller Teil
NH +
H
120
O
O Me
24a
Cl -
C6H12ClNO2, 165.62 g/mol
1 H-NMR (300 MHz, CDCl3): = 1.95-2.19 (m, 3H), 2.30-2.45 (m, 1H), 3.38-3.62 (m, 2H), 3.77 (s, 3H,
CH3), 4.36-4.49 (m, 1H), 9.21 (s (br), 1H, NH2), 10.64 (s (br), 1H, NH2) ppm.
13 C-NMR (75.5 MHz, CDCl3): = 23.6 (NCH2CH2), 28.7 (CHCH2), 45.8 (NCH2), 53.4 (OCH3), 59.2
(NCH), 169.2 (COO) ppm.
TG: 97.7 °C (onset: 54.3 °C)
20
Drehwert (DCM): []D = -50.4 °
N-Methyl-L-(-)-Prolin-methylester-chlorid 24b
Ausbeute: 95.3 % (4.1 g, 22.9 mmol)
NH +
Me
24b
O
O Me
Cl -
C7H14ClNO2, 179.64 g/mol
1 H-NMR (300 MHz, [D6]-DMSO): = 1.84-1.96 (m, 1H), 1.98-2.14 (m, 2H), 2.32-2.48 (m, 1H), 2.91 (s,
3H, CH3), 3.07-3.27 (m, 1H), 3.54-3.67 (m, 1H), 3.75 (s, 3H, CH3), 4.41-4.54 (m, 1H), 11.2 (s (br), 1H,
NH) ppm.
13 C-NMR (75.5 MHz, [D6]-DMSO): = 21.5 (NCH2CH2), 27.1 (CHCH2), 44.9 (NCH2), 52.9 (CH od.
CH3), 58.2 (CH od. CH3), 66.1 (CH3), 168.0 (COO) ppm.
TG: 72.9 °C (onset: 44.0 °C)
20
Drehwert (DCM): []D = -72.9 °