4-Piperidinecarboxylic acid → 1-Carbobenzoxy-4-piperidinecarboxylic Acid
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>>[CH2:14]([O:13][C:11]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Participants
Procedure
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).
Sources & evidence
- ORD record
- ord-baf068db8dcd4e049b680cf65a3c10fc
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04977159
Reaction notes
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