Process for synthesis of azetidine and novel intermediates there

Details Process for synthesis of azetidine and novel intermediates there Process for synthesis of azetidine and novel intermediates there

1987-01-28

1989-09-26

Shah, Mukund J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548950, C07D20504

Patent

active

048701890

ABSTRACT:
A novel process is described for preparing azetidine and 2 or 3 methyl and ethyl azetidine free bases by reacting primary arylmethylamine having suitable bulk providing substituents attached to the methyl carbon and an appropriate propane derivative having leaving groups in the one and three position in hot organic solvent containing a non-nucleophilic base and an amount of water sufficient to promote azetidine ring formation to give N-protected-azetidines and deprotecting by hydrogenolysis under acidic conditions to give an acid salt of the azetidines and thereafter flashing off vaporized azetidine from a hot, agitated strong base solution or slurry and condensing to give the liquid azetidine free bases.

REFERENCES:
patent: 3336294 (1967-08-01), Miller et al.
patent: 4529544 (1985-07-01), Renga
patent: 4634554 (1987-01-01), Wood et al.
Nitta and Kanamori, "Synthesis of Azetidine from 1-Substituted Azetidin-3-ols", Heterocycles, vol. 24, No. 9, 1986, pp. 2467-2470.
Szmuszkovicz et al., "New Synthesis of Azetidine", J. Org. Chem. 1981, 46, 3562-3564.

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