Cyclization of 1-alkylamino-3-halo-2-alkanols to 1-alkyl-3-azetidinols

✍ Scribed by V.R. Gaertner

• Publisher: Elsevier Science
• Year: 1966
• Tongue: French
• Weight: 182 KB
• Volume: 7
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)72925-x

✦ Synopsis

We describe here a simple two-step synthesis of l-alkyl-3-azetldlnols, whereby this new series becomes the most readily prepared class of azetidlnes. The method points to a general conversion of complex primary amines to 3-azetldlnols, as well as providing an entree into the 3-substituted azetldines. The four-membered trlmethylenelmlne ring is considered to be the most difficultly closed of the slmple nitrogen heterocycles (1).

The unstable Intermediates, 1-alkylamlno-3-chloro-2-propanols (l_), obtained from primary amlnes and eplchlorohydrin

(2), spontaneously cycllzed to 1-alkyl-3-azetldinol (2) hydrochlorides.