N-substituted azetidine carboxylate derivatives

Details N-substituted azetidine carboxylate derivatives N-substituted azetidine carboxylate derivatives

1988-06-09

1989-08-08

Sutto, Anton H.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

204 78, C07D20504

Patent

active

048554529

ABSTRACT:
Process for the preparation of a compound of formula or a salt thereof ##STR1## wherein R.sub.1 represents a hydrogen atom or a group of formula R.sub.2 SO.sub.2 or phenyl--CH(R.sub.3)-- wherein R.sub.2 represents a phenyl, tolyl or C.sub.1-4 alkyl group and R.sub.3 represents a hydrogen atom or a phenyl or C.sub.1-4 alkyl group, which process comprises contacting nickel in an oxidation state of at least 3 with a 3-hydroxymethyl azetidine derivative of formula ##STR2## wherein R.sub.4 represents a group of formula R.sub.2 SO.sub.2 or phenyl--CH(R.sub.3)-- and R.sub.5 represents a hydrogen atom or a hydroxymethyl group or a group of formula COOH or a salt thereof, followed, where R.sub.5 is not a hydrogen atom, by the decarboxylation of the compound of the 3,3-dicarboxylic intermediate product or a salt thereof and, if desired to produce a compound in which R.sub.1 represents a hydrogen atom, by deprotection of the N-atom. Also, novel N-substituted azetidine carboxylate derivatives of the formula ##STR3## wherein X represents a group CH.sub.2 OH or COOY where Y represents a hydrogen or an alkali or alkaline earth metal atom.

REFERENCES:
patent: 4496440 (1985-01-01), Campbell et al.
Blum et al., Acta. Chem. Scand., 338, (1981) pp. 739-741.
Campbell et al., Chem. Abstracts, 102 (1985) 122076Z.
Fieser & Fieser, Reagents for Organic Synthesis, John Wiley & Sons (1967) pp. 731-732.
Kwait et al., Chem. Abstracts, 90, (1979) 54231c.

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