Jozef Hodyl PhD Thesis - Theses - Flinders University

1,4,7-tris-((S)-2-hydroxy-3-phenoxypropyl)-1,4,7,10-tetraazacyclododecane, 46HHOOOHHONNHNNHOHO46To a stirred suspension of Pd/C catalyst, (10%, 500 mg), in absolute ethanol (10cm 3 ), a solution of 71 (523 mg, 0.69 mmol) dissolved in absolute ethanol (5 cm 3 )was added. The mixture was stirred for 5 min. and then cyclohexene, 74, (283 mg,3.45 mmol), was added. The mixture was stirred under gentle reflux for 5 h, cooledto room temperature and filtered through a small celite column and washed withabsolute ethanol (5 cm 3 ). The product was concentrated in vacuo to give 46 as abrown viscous oil, yield 426 mg, quantitative. 13 C NMR (CDCl 3 ): δ 158.70 ( 2 C, Ar,ipso); 158.62 ( 1 C, Ar, ipso); 129.31 (4 C, Ar); 129.28 (2 C, Ar); 120.73 (2 C, Ar);120.64 (1 C, Ar); 114.63 (4 C, Ar); 114.45 (2 C, Ar); 69.88 (2 C, OCH 2 ); 69.23 (1 C,OCH 2 ); 65.45 (2 C, CH); 65.24 (1 C, CH); 58.60 (2 C, CH 2 N); 58.24 (1 C, CH 2 N);51.33 (2 C, cyclen -CH 2 ); 49.79 (2 C, cyclen -CH 2 ); (2 C, cyclen -CH 2 ); 44.33 (2 C,cyclen -CH 2 ).138