Synthesis and aqueous chemistry of alpha-acetoxy-N-nitrosomorpholine: Reactive intermediates and products

Alpha-acetoxy-N-nitrosomorpholine is synthesized starting by the anodic oxidation of N-acetylorpholine in methanol. The 55% yield of N-nitrosomorpholinic acid, after cyanide-for-methoxy group exchange and hydrolysis, is an improvement of 10-fold over the original 10-step method, and this is readily converted to alpha-acetoxy-N-nitrosomorpholine.