Abstract
Using the synthesis of 1,2-bis(methylamino)ethane-1,2-diol dihydrochloride (5) as an example, it was demonstrated that aliphatic α-aminocarbinols can be stabilized as hydrochlorides. The reaction of compound 5 with N-chloromethylamine in CHCl3 in the presence of K2CO3 afforded 1,2,1",2"-tetramethyl-3,3"-bidiaziridine as a mixture of diastereomers (a racemate and a meso form). The meso form was isolated in the individual state and its structure was established by X-ray diffraction analysis. The kinetics of inversional epimerization was studied.
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Petukhova, V.Y., Makhova, N.N., Ananikov, V.P. et al. 1,2-Bis(methylamino)ethane-1,2-diol dihydrochloride as a new precursor of 1,2,1",2"-tetramethyl-3,3"-bidiaziridine. Russian Chemical Bulletin 53, 641–646 (2004). https://doi.org/10.1023/B:RUCB.0000035650.08227.36
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DOI: https://doi.org/10.1023/B:RUCB.0000035650.08227.36