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The synthesis of deuterium-labeled N-nitrosodiethanolamine and N-nitroso-2-hydroxymorpholine

✍ Scribed by Richard N. Loeppky; Heping Xiong

Book ID
102901510
Publisher
John Wiley and Sons
Year
1994
Tongue
French
Weight
619 KB
Volume
34
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Two deuterated derivatives of N‐nitrosodiethanolamine and two deuterated derivatives of N‐Nitroso‐2‐hydroxymorpholine were prepared. 1,1,1′,1′‐^2^H~4~‐N‐Nitrosodiethanolamine 1a was prepared in 99% isotopic purity by simple base catalyzed H‐D exchange. 2,2,2′,2′‐^2^H~4~‐N‐Nitrosodiethanolamine 1b was synthesized in 98% isotopic purity by the LiAlD~4~ reduction of dimethyl iminodiethanoate, followed by acid catalyzed nitrosation. 5,5‐^2^H~2~‐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 CH~2~ adjacent to the ester function of 2,2‐diethoxyethylcarboethoxymethylnitrosamine, 2) its reduction with diisobutylaluminum hydride at −8°C followed by 3) acid catalyzed hydrolysis of the acetal and cyclization to the hemiacetal. 2‐^2^H‐N‐Nitroso‐2‐hydroxymorpholine 2b (98% isotopic purity) was prepared through the LiAlD~4~ reduction of 2‐hydroxyethylcorboethoxymethylnitrosamine at −78°C.

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