Ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate Argatroban Intermediate CAS 74892-82-3 NT

Ethyl (2R,4R)-4-methyl-2-piperidinecarboxylate (CAS 74892-82-3) is a chiral piperidine derivative featuring an ethyl ester and a methyl substituent at the 4-position, with stereocenters in the (2R,4R) configuration . This compound is also known as Argatroban Impurity 27 and serves as a key intermediate in the synthesis of Argatroban (A769000), a direct thrombin inhibitor used as an anticoagulant .

Chemical Characteristics:

• Features a piperidine ring with defined (2R,4R) stereochemistry

• Contains an ethyl ester functional group and a methyl substituent at the 4-position

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• Molecular formula: C₉H₁₇NO₂

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• Molecular weight: 171.24 g/mol 

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• Boiling point: 226.1±33.0°C (Predicted) 

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• Density: 0.969±0.06 g/cm³ (Predicted) 

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• pKa: 6.65±0.10 (Predicted) 

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• Solubility: Sparingly soluble in chloroform, slightly soluble in ethanol, soluble in methanol 

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• Storage: Keep in dark place, sealed in dry, store in freezer under -20°C 

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Role in Argatroban Synthesis:

Argatroban is a synthetic direct thrombin inhibitor approved for the prophylaxis and treatment of thrombosis in patients with heparin-induced thrombocytopenia (HIT). This compound serves as a key chiral building block in the multi-step synthesis of the API, introducing the stereochemically defined piperidine core structure essential for the drug's biological activity. As Argatroban Impurity 27, it is also used as a reference standard for quality control and analytical method development .

Key Features:

• High Purity: ≥ 98% (HPLC) with enantiomeric excess of 96% 

• Chiral Building Block: Defined (2R,4R) configuration

• Well-characterized with available analytical data

• Suitable for pharmaceutical synthesis and impurity reference applications

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Applications:

• Pharmaceutical R&D: As a key intermediate in the synthesis of Argatroban API and other piperidine-based therapeutics

• Quality Control: Serves as a reference standard for impurity profiling and analytical method development (AMV) in Argatroban production

• Regulatory Submissions: Used in ANDA and DMF filings for Argatroban-related drug products

• Asymmetric Synthesis: Employed in designing peptidomimetics and CNS-targeted agents, supporting structure–activity relationship (SAR) studies and drug optimization 

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Packaging: ___ (e.g.: 1g, 5g, 10g per package, as per customer's request)

Storage: Powder: -20°C for up to 3 years; 4°C for up to 2 years. In solvent: -80°C for 6 months; -20°C for 1 month. Protect from light and moisture

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