Process for producing tetrahydroisoquinoline-3-carboxylic acid c

Details Process for producing tetrahydroisoquinoline-3-carboxylic acid c Process for producing tetrahydroisoquinoline-3-carboxylic acid c

1995-04-04

1997-02-11

Davis, Zinna Northington

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D21726

Patent

active

056022557

ABSTRACT:
The present invention relates to a process for producing 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid compounds or salts thereof represented by the following formula (II): ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently represent hydrogen, hydroxy or lower alkoxy, and R.sup.4 represent hydrogen, lower alkyl, aryl or aralkyl, the process comprising, allowing phenylalanine compounds to react with formaldehyde or paraformaldehyde in the presence of sulfuric acid or hydrobromic acid, the phenylalanine compounds being represented by the following formula (I): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the same meaning as defined above.

REFERENCES:
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"Bis(Chloromethyl)Ether--Chemical and Physical Data" IARC Monographs, 4, pp. 231-238 (1974).
B. L. Van Duuren et al., "bis(Chloromethyl) Ether", Org. Syn., Coll. vol. 4, pp. 101-103 (1963).
Robert R. Sealock et al., "The Synthesis, Resolution . . . " J. Amer. Chem. Soc., 73, pp. 5386-5389 (1951).
Paul L. Ornstein et al., "Synthesis of 6-Oxodecahydroisoquinoline-3-carboxylates . . . ", J. Org. Chem 56, pp. 4388-4392 (1991).
Kazmierski et al, J. Med. Chem., 1988, vol. 31, No. 11, pp. 2170-2177.

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