Process for producing threo-3-(3,4-dihydroxyphenyl)serine

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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562401, 562446, C07C 1900, C07C 2000, C07D31754, C07D31758

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active

044801092

ABSTRACT:
A process for producing an optically active threo-3-(3,4-dihydroxyphenyl)serine represented by the formula ##STR1## which is useful as a remedy for peripheral orthostatic hypotension or as an antidepressant, which process comprises treating threo-3-(3,4-methylenedioxyphenyl)serine or an N-carbobenzoxy derivative thereof represented by the formula ##STR2## wherein A represents a hydrogen atom or a carbobenzoxy group, with a Lewis acid to form threo-3-(3,4-dihydroxyphenyl)serine or an N-carbobenzoxy derivative thereof represented by the formula ##STR3## wherein A is as defined above, and, if A is a carbobenzoxy group, catalytically reducing the resulting compound of formula [2]; a racemic or optically active threo-N-carbobenzoxy-3-(3,4-methylenedioxyphenyl)serine represented by the formula ##STR4## which is a novel compound useful as an intermediate in the above synthesis; and a process for producing said novel compound.

REFERENCES:
patent: 3679694 (1972-07-01), Rambacher et al.
patent: 3920728 (1975-11-01), Hegedus et al.
patent: 4246428 (1981-01-01), Ohashi et al.
patent: 4319040 (1982-03-01), Ohashi et al.

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