K. Fukatsu, N. Fujii, S. Ohkawa
Apr 23, 1999
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Journal
Tetrahedron-asymmetry
Abstract
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.