129348-88-5Relevant academic research and scientific papers
A novel electrochemical method for benzoylation of aminoalcohols with methyl benzoates at room temperature
Arai, Kenji,Tamura, Shohei,Masumizu, Tatsuya,Kawai, Ken-Ichi,Nakajima, Shoichi,Ueda, Akira
, p. 903 - 907 (2007/10/02)
A novel electrochemical method of benzoylating aminoalcohols 2 by use of methyl benzoates 1 at room temperature was developed. 2-Aminoethanols 2 (n=0, R3=H) and 3-aminopropanols 2 (n=1, R3=H) gave the corresponding benzamides 4, as a result of electrochemical transesterification followed by O,N-acyl migration.In contrast, o- and m-aminobenzylalcohols (7a and 7b) and trans-4-(aminomethyl)cyclohexanemethanol (8a) afforded the corresponding benzoic esters, since their acyl migration is hindered.A local anesthetic, procaine, was prepared by using this electrochemical reaction.A mechanism for electrochemical transesterification, which involves a formation of alcoholate anion by a one-electron reduction of alcohol, is presented.
