title: Stereoselective Synthesis of (R)-3-Methylthalidomide by Piperidin-2-one Ring Assembly Approach.
abstract: A simple and stereoselective synthesis of 3-methylthalidomide, a configurationally stable thalidomide analog, is presented. Herein we describe the synthesis of (R)-3-methylthalidomide starting from (S)-alanine by piperidin-2-one ring assembly approach in high yield and enantiomeric purity without using a chiral auxiliary or reagent. Starting from (R)-alanine, the corresponding (S)-3-methylthalidomide can be prepared using the same methodology.
authors.affiliation: Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, India.
authors.forename: Shyam Raj
authors.initials: SR
authors.lastname: Yadav
authors.affiliation: Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, India.|Academy of Scientific and Innovative Research, New Delhi, India.
authors.forename: Vinay Shankar
authors.initials: VS
authors.lastname: Tiwari
authors.affiliation: Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, India.|Academy of Scientific and Innovative Research, New Delhi, India.
authors.forename: Wahajul
authors.initials: W
authors.lastname: Haq
mesh_terms: D060326:Chemistry Techniques, Synthetic; D006863:Hydrogen-Ion Concentration; D010880:Piperidines / Q000737:chemistry*; D010881:Piperidones / Q000737:chemistry*; D013237:Stereoisomerism; D013792:Thalidomide / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C114058:3'-methylthalidomide; D010880:Piperidines; D010881:Piperidones; D013792:Thalidomide; C032727:piperidine; C043384:2-piperidone
keywords: enantioretentive alkylation; oxazolidinone; teratogenic; thalidomide; tumor necrosis factor-α