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Efficient synthesis of azetidine through N ‐trityl‐ or N ‐dimethoxytritylazetidines starting from 3‐amino‐l‐propanol or 3‐halopropylamine hydrohalides
Author(s) -
Huszthy Peter,
Bradshaw Jerald S.,
Krakowiak Krzysztof E.,
Wang Tingmin,
Dalley N. Kent
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300506
Subject(s) - azetidine , chemistry , anhydrous , base (topology) , chloride , salt (chemistry) , organic chemistry , mathematical analysis , mathematics
Efficient synthetic routes for the preparation of azetidine starting from commercially available 3‐amino‐l‐propanol or 3‐halopropylamine hydrohalides are reported. First, the appropriate N ‐trityl‐ or N ‐dimethoxy‐trityl 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.