Synthesis of TAK-218 using (R)-2-methylglycidyl tosylate as a chiral building block |
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| Institution: | 1. School of Postgraduate Studies and Research, International Medical University, Kuala Lumpur, Malaysia;2. Department of Pharmaceutical Chemistry, School of Pharmacy, International Medical University, Kuala Lumpur, Malaysia;3. Head, Centre for Bioactive Molecules and Drug Delivery, Institute for Research, Development and Innovation (IRDI), International Medical University, Kuala Lumpur, Malaysia;1. Shanghai Key Laboratory of Bioactive Small Molecules, Department of Pharmacology, School of Pharmacy, Fudan University, Shanghai 201203, China;2. State Key Laboratory of Quality Research in Chinese Medicine and School of Pharmacy, Macau University of Science and Technology, Macau, China |
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| Abstract: | We performed an asymmetric synthesis of (S)-2,3-dihydro-2,4,6,7-tetramethyl-2-(4-phenyl-1-piperidinyl)methyl]-5-benzofuranamine dihydrochloride (TAK-218, 1), a compound used for the treatment of traumatic and ischemic central nervous system injuries. Oxirane 6, which was synthesized from (R)-2-methylglycidyl tosylate, was treated with aqueous trifluoroacetic acid to afford benzofuranmethanol 7 with inversion of stereochemistry at the stereogenic center. Compound 7 was converted into 1 with high enantiomeric excess in four steps. |
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