Preparation of 4-phenyl-1,2,3,6-tetrahydropyridines

Details Preparation of 4-phenyl-1,2,3,6-tetrahydropyridines Preparation of 4-phenyl-1,2,3,6-tetrahydropyridines

1999-06-16

2000-10-24

Chang, Ceila

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546113, C07D21174, C07D491044

Patent

active

061369810

ABSTRACT:
A process for the preparation of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, R.sub.2 and R.sub.4 are alkyl of 1 to 4 carbon atoms and R.sub.3 is alkyl of 1 to 8 carbon atoms comprising reacting a compound of the formula ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are defined as above or an amine salt thereof with an electrophilic halogenating agent to obtain a compound of the formula ##STR3## wherein Hal.sub.1 is halogen, reacting the latter with a halohydroxylating agent to obtain a compound of the formula ##STR4## wherein Hal.sub.2 is halogen, reacting the latter with a base to obtain a compound of the formula ##STR5## reacting the latter with a diastereoselective reducing agent to obtain a compound of the formula ##STR6## reacting the latter with a reducing agent to obtain a cis racemic compound of formula I and optionally resolving the latter with a resolution agent to obtain the desired optical form and novel intermediates.

REFERENCES:
patent: 4132710 (1979-01-01), Gauthier et al.
Kubela et al. "4-Arylpiperidine derivatives" CA 90:203872, 1977.
Ramachandra et al, "An Antiinflammatory . . . Synthesis", Tetrahedraon, vol. 44, No. 7, (1988) pp. 2081-2086.
Nagai et al, "Studies . . . Compounds", Chem. Pharm. Bull., vol. 28, No. 5, (1980) pp. 1387-1393.
Lyle, et al, "Nucleophilic . . . Epoxypiperidine", J. Org. Chem., vol. 32, No. 9, (1967) pp. 2873-2875.

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