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

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

C - Chemistry, Metallurgy

07

D

260/516.3

C07D 317/60 (2006.01)

Patent

CA 1201723

ABSTRACT OF THE DISCLOSURE A process for producing an optically active threo-3-(3,4-dihydroxyphenyl)serine represented by the formula Image [1] 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 Image [3] wherein A represents a hydrogen atom or a carbobenzoxy group, with a Lewis acid to form threo-3-(3,4-dihydroxy- phenyl)serine or an N-carbobenzoxy derivative thereof represented by the formula [2] Image wherein A is as defined above, and, if A is a carbo- benzoxy 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 Image [3"] which is a novel compound useful as an intermediate in the above synthesis; and a process for producing said novel compound.

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