Journal of Heterocyclic Chemistry p. 1197 - 1207 (1993)
Update date:2022-07-30
Topics: Deprotection Protection of Amino Group Azetidine Ring Formation
Huszthy
Bradshaw
Krakowiak
Wang
Dalley
Efficient synthetic routes for the preparation of azetidine starting from commercially available 3-amino-1-propanol or 3-halopropylamine hydrohalides are reported. First, the appropriate N-trityl- or N-dimethoxytrityl protected tosyloxy- or halopropylamines were prepared. These precursors were then cyclized into the N-trityl- or N-dimethoxytritylazetidines. The N-protecting groups were removed in the presence of perchloric acid giving the hydrogen perchlorate salt of azetidine. The latter compound was transformed into its free base using a strong base under anhydrous conditions. The relatively expensive 4,4'-dimethoxytrityl chloride and less expensive trityl chloride used in these synthetic procedures were recycled in good yields. Azetidine hydrogenperchlorate can be used to prepare N-substituted azetidines without the need to isolate the free azetidine.
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Doi:10.1021/jm00072a014
(1993)Doi:10.1002/ardp.19943270214
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(1993)Doi:10.1016/j.ejmech.2005.07.005
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(1993)Doi:10.1016/j.bmcl.2007.08.042
(2007)