58880-34-5Relevant academic research and scientific papers
The synthesis of Deuterium-Labeled N-Nitrosodiethanolamine and N-Nitroso-2-hydroxymorpholine
Loeppky,Xiong
, p. 1099 - 1110 (1994)
Two deuterated derivatives of N-nitrosodiethanolamine and two deuterated derivatives of N'-Nitroso-2-hydroxymorpholine were prepared. 1,1,1',1'-2H4-N-Nitrosodiethanolamine 1a was prepared in 99% isotopic purity by simple base catalyzed H-D exchange. 2,2,2',2'-2H4-N-Nitrosodiethanolamide 1b was synthesized in 98% isotopic purity by the LiAlD4 reduction of dimethyl iminodiethanoate, followed by acid catalyzed nitrosation. 5,5-2H2-N-Nitroso-2-hydroxymorpholine 2a was prepared in 99% isotopic purity through a series of steps involving 1) the selective base catalyzed H-D exchange of the CH2 adjacent to the ester function of 2,2-diethoxyethylcarboethoxymethylnitrosamine, 2) its reduction with diisobutylaluminum hydride at 78°C followed by 3) acid catalyzed hydrolysis of the acetal and cyclization to the hemiacetal. 2-2H-N-Nitroso-2-hydroxymorpholine 2b (98% isotopic purity) was prepared through the LiAlD4 reduction of 2-hydroxyethylcorboethoxymethylnitrosamine at -78°C.
