339183-94-7Relevant articles and documents
Efficient Diastereoselective Three-Component Synthesis of Pipecolic Amides
van der Heijden, Gydo,van Schaik, Timo B.,Mouarrawis, Valentinos,de Wit, Martin J. M.,Velde, Christophe M. L. Vande,Ruijter, Eelco,Orru, Romano V. A.
, p. 5313 - 5325 (2019/06/10)
An efficient Ugi-type three-component reaction (U-3CR) for the synthesis of pipecolic amides is reported. The U-3CR between electronically diverse isocyanides, carboxylic acids and 4-substituted Δ1-piperideines proceeds in a highly diastereoselective fashion. The Δ1-piperideines are obtained by NCS-mediated oxidation of the corresponding 4-substituted piperidines, which in turn are generated by an efficient two-step procedure involving the alkylation of 4-picoline and subsequent catalytic hydrogenation of the pyridine ring. We demonstrate the utility of this U-3CR, in combination with the convertible isocyanide 2-bromo-6-isocyanopyridine, in the synthesis of the anticoagulant argatroban.
Direct diastereoselective synthesis of (±)-cis- and (±)-trans-4-methylpipecolic acid and derivatives
Cossy, Janine,Belotti, Damien
, p. 2119 - 2120 (2007/10/03)
(±)-cis- or (±)-trans-4-Methylpipecolic acid and ester derivatives can be obtained directly by addition of electrophiles to α-lithiated N-Boc 4-methylpiperidine.
A short synthesis of argatroban: A potent selective thrombin inhibitor
Cossy, Janine,Belotti, Damien
, p. 1989 - 1992 (2007/10/03)
Argatroban was synthesized in seven steps from 4-methylpiperidine. The condensation of (±)-trans-benzyl 4-methylpipecolic acid ester with Nα-Boc-Nω-nitro-L-arginine led to two diastereomers that were separated. One of them is the precursor of argatroban.
