Process for preparing azetidine derivatives; and intermediates t

Details Process for preparing azetidine derivatives; and intermediates t Process for preparing azetidine derivatives; and intermediates t

1986-04-16

1988-10-18

Rizzo, Nicholas S.

Chemistry: electrical and wave energy

Processes and products

548953, B01J 1908, C07D20504

Patent

active

047785772

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 of 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:
Campbell, et al., Chem. Abstracts, 102, (1985), entry 122076z.
Fieser & Fieser, Reagents for Organic Synthesis, John Wiley & Sons (1967) pp. 731-732.
Kwart, et al., Chem. Abstracts, 90, (1979), entry 54231c.
Blum et al., Acta. Chem. Scand., 338, (1981), pp. 739-741.

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