4-Piperidinecarboxylic acid → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

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Reaction Steps

Scheme 1 illustrates an example of a route for the preparations of compounds of formula (VI) and (VII). 4-Piperidinecarboxylic acid of formula (II) is first reacted with benzyl chloroformate, in the presence of a base and in an aqueous medium, to obtain 1-(benzyloxy-carbonyl)-4-piperidinecarboxylic acid of formula (III). 1,2,3,4-tetrahydro-9-H-pyrido[3,4-b]indole is reacted with the acid chloride of the compound of formula (III), prepared in situ with a chlorinating agent, for example thionyl chloride, in an inert solvent, for example tetrahydrofuran, and in the presence of a base, for example triethylamine, at about room temperature, to obtain benzyl 4-[(1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indol-2-yl)-carbonyl]-1-piperidinecarboxylate of formula (V). The compound of formula (V) is subjected to a catalytic reduction to obtain the compound of formula (VI).

Provenance & Evidence