Synthesis of terfenadine and derivatives

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

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546240, C07D21122, C07D21134

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active

059257610

ABSTRACT:
Processes for preparing compounds having the general formula: ##STR1## wherein R.sup.1a is protected carboxy, carboxy, hydroxymethyl, protected hydroxymethyl, or methyl are disclosed. Processes of the invention begin with a starting material of the general formula II ##STR2## and elaborate the product by reductive amination of an aldehyde of formula IVa ##STR3## with .alpha.,.alpha.-diphenyl-4-piperidinemethanol.

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Maillard et al. "Anti-inflammatories derives de l'acide . . . " Chimie Therapeutique 8, 487-494 (1973).
Carr et al. "Synthesis of Terfenadine" Arzneim.-Forsch. 32, 1157-1159 (1982).
Kawai et al. "A Facile Synthesis of an Oxidation Product of Terfenadine" J. Or. Chem. 59, 2620-2622 (1994).
W. Theilheimer Synthetic Methods of Organic Chemistry 26, 192 (1972).
morrison and Boyd "Organic chemistry" p. 261, 1973.
Linan Castellet et al. "Terfenadine" CA 105:226360 (same reference abstracted by WPIDS), 1985.
Morrison and Boyd "Organic Chemistry" pp. 642, 675, 1973.
Greene "Protective ghroups of organic synthesis" pp. 185, 187, 1982.

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