2-Aminocyclopentanecarboxamides
1083
Colourless crystals; m.p.: 146±148ꢀC ꢀEtOAc); 1H NMR ꢀCDCl3): ꢁ 1.40 ꢀs, 3 Â CH3),
1.48±2.14 ꢀ3 Â CH2), 2.82 ꢀm, H-1), 4.11 ꢀqui, J 7.8, H-2), 4.41 ꢀAB system, J 8 Hz, coup. with
NH, NHCH2Ph), 5.10 ꢀb, CONHCH2), 6.05 ꢀbs, NHCOO), 7.20±7.38 ꢀm, 5 Â CH) ppm; 13C NMR
ꢀCDCl3): ꢁ 23.3 ꢀC4), 28.8 ꢀC5), 29.1 ꢀ3 Â CH3), 33.3 ꢀC3), 44.3 ꢀNCH2Ph), 48.7 ꢀC1), 54.9 ꢀC2),
79.9 ꢀOCꢀCH3)3), 128.1 ꢀPh, C40), 128.4 ꢀPh, C30, C50), 129.4 ꢀPh, C20, C60) 138.9 ꢀPh, C10), 156.6
ꢀNHCOO), 174.3 ꢀCHCON) ppm.
cis-N-Benzyl-2-aminocyclopentanecarboxamide ꢀ13; C13H19ClN2O)
cis-N-Benzyl-2-tert-butoxycarbonylaminocyclopentanecarboxamide ꢀ12; 0.7 g, 2.2 mmol) was
dissolved in a 3 M HCl solution in 20 cm3 dryEtOH. The reaction mixture was left to stand at
room temperature for 2 h and evaporated at room temperature. The 0.44 g obtained white crystalline
powder ꢀ78%) were puri®ed byrecrystallization.
Colourless crystals; m.p.: 150±153ꢀC ꢀi-Pr2O); 1H NMR ꢀCDCl3): ꢁ 1.70±2.28 ꢀ3 Â CH2), 3.04
ꢀm, H-1), 3.87 ꢀm, H-2), 4.41 ꢀAB, J 15.3, NHCH2Ph), 5.10 ꢀb, CONHCH2), 7.34±7.45 ꢀm,
5 Â CH) ppm; 13C NMR ꢀCDCl3): ꢁ 21.9 ꢀC4), 28.7 ꢀC5), 30.6 ꢀC3), 43.3 ꢀNCH2Ph), 46.1 ꢀC1),
53.9 ꢀC2), 127.6 ꢀPh, C30, C50), 127.9 ꢀPh, C40), 129.3 ꢀPh, C20, C60), 138.3 ꢀPh, C10), 175.0
ꢀCONH2) ppm.
Acknowledgements
We express thanks to the Hungarian Scienti®c Research Foundation for grants OTKA F032355 and
T030452.
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