Efficient synthesis of azetidine through N-trityl- or N- dimethoxytritylazetidines starting from 3-amino-1-propanol or 3- halopropylamine hydrohalides
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.
Huszthy,Bradshaw,Krakowiak,Wang,Dalley
p. 1197 - 1207
(2007/10/02)
A NEW METHOD TO EXTEND DIMERCAPTAN ODER DIAMINE CHAINS WITH AMINOPROPYL UNITS USING 3-BROMO-N-TRITYLPROPANAMINE
Dimercaptans and diamines react with 3-bromo-N-tritylpropanamine to give the corresponding N,N'-ditrityldithia and N,N'-ditritylpolyaza compounds in yields of 50-80percent.The trityl protecting group are readily removed in acid.These reactions make possib
Krakowiak, Krzysztof E.,Huszthy, Peter,Bradshaw, Jerald S.,Izatt, Reed M.
p. 21 - 22
(2007/10/02)
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