Diethyl Ether → 1,7-Bis(tert-butoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane

Participants

Reaction Steps

To a solution of compound (19) (8.52 g, 12.74 mmol) in ethanol (130 ml) was added 10% Pd/C (2.6 g). The resultant mixture was stirred at an ambient temperature in the presence of H2 (g) for 12 hours. The reaction mixture was filtered through a celite pad and washed with ethanol (2×20 ml). The filtrate was evaporated in vacuo to give an oily residue, which was then treated with Et2O to obtain a white solid of compound (20) (4.85 g, 97% yield). 1H NMR (500 MHz, CD3OD): δ 3.44 (s, 4H), 2.91 (s, 16H), 1.47 (s, 18H); 13C NMR (125 MHz, CD3OD): δ 173.0, 82.8, 57.4, 52.2, 46.5, 28.5; HRMS (FAB) calculated for C20H41N4O4: 401.3128 [(M+H)+], measured value: 401.3132 [(M+1-1)+].

Provenance & Evidence