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Approaches to the Preparation of Enantiomerically Pure (2 R ,2′ R )‐(+)‐ threo ‐Methylphenidate Hydrochloride
Author(s) -
Prashad Mahavir
Publication year - 2001
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200107)343:5<379::aid-adsc379>3.0.co;2-4
Subject(s) - enantioselective synthesis , chemistry , enantiomer , epimer , diastereomer , stereochemistry , amide , resolution (logic) , hydrochloride , organic chemistry , catalysis , computer science , artificial intelligence
Various approaches to the preparation of enantiomerically pure (2 R ,2′ R )‐(+)‐ threo ‐methylphenidate hydrochloride ( 1 ) are reviewed. These approaches include synthesis using enantiomerically pure precursors obtained by resolution, classical and enzyme‐based resolution approaches, enantioselective synthesis approaches, and approaches based on enantioselective synthesis of (2 S ,2′ R )‐ erythro ‐methylphenidate followed by epimerization at the 2‐position. 1 Introduction 2 Methods for the Enhancement of Enantiomeric Purity of 1 3 Approaches Using Enantiomerically Pure Precursors Obtained by Resolution 4 Classical Resolution Approaches 4.1 Resolution of Amide and Acid Derivatives 4.2 Resolution of (±)‐ threo ‐Methylphenidate 5 Enzyme‐Based Resolution Approaches 6 Enantioselective SynthesisApproaches 7 Approaches Based on Enantioselective Synthesis of (2 S ,2′ R )‐ erythro ‐Methylphenidate and Epimerization 8 Conclusions