339183-92-5

Usage

Uses

Used in Pharmaceutical Industry:
BENZYL (+/-)-TRANS-N-BOC-4-METHYL-PIPERIDINE-2-CARBOXYLATE is used as a synthetic intermediate for the production of Argatroban (A769000), a direct thrombin inhibitor. BENZYL (+/-)-TRANS-N-BOC-4-METHYL-PIPERIDINE-2-CARBOXYLATE plays a crucial role in the development of medications that help manage heparin-induced thrombocytopenia, a serious blood clotting disorder.
In the synthesis of Argatroban, BENZYL (+/-)-TRANS-N-BOC-4-METHYL-PIPERIDINE-2-CARBOXYLATE contributes to the formation of the final product, which is an essential drug for patients experiencing complications from heparin treatment. By facilitating the synthesis of Argatroban, BENZYL (+/-)-TRANS-N-BOC-4-METHYL-PIPERIDINE-2-CARBOXYLATE has a significant impact on the pharmaceutical industry and the treatment of heparin-induced thrombocytopenia.

Upstream product

• 123387-50-8 4-methylpiperidine-1-carboxylic acid tert-butyl ester 
• 501-53-1 benzyl chloroformate 
• 626-58-4 4-methylpiperidin 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant academic research and scientific papers

Efficient Diastereoselective Three-Component Synthesis of Pipecolic Amides

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

(±)-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

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.