Short Synthesis of Methylphenidate and Its p-Methoxy Derivative

REFERENCES AND NOTES

• Budavari , S. , ed. 1989 . The Merck Index, , 11th ed. , 960 Rahway : Merck . and references cited therein
   Google Scholar
• Froimowitz , M. , Patrick , K. S. and Cody , V. 1995 . Pharm. Res. , 12 : 1430
   PubMedGoogle Scholar
• Thai , D. L. , Sapko , M. T. , Reiter , C. T. , Bierer , D. E. and Perel , J. M. 1998 . J. Med Chem. , 41 : 591 For the first stereogenic synthesis of methylphenidate and its p-derivatives, see
   PubMed Web of Science ®Google Scholar
• Deutsch , H. M. , Shi , Q. , Gruszecka-Kowalik , E. and Schweri , M. 1996 . J. Med. Chem. , 39 : 1201 For recent racemic synthesis of methylphenidate, see
   PubMed Web of Science ®Google Scholar
• Pan , D. , Gatley , S. J. , Dewey , S. L. , Chen , R. and Alexoff , D. A. 1994 . Eur. J. Pharmacol. , 264 : 177
   PubMed Web of Science ®Google Scholar
• Patrick , K. S. , Ellington , K. R. and Breese , G. R. 1984 . J. Pharmacol. Exp. Ther. , 231 : 61
   PubMed Web of Science ®Google Scholar
• Pannizzon , L. 1944 . Helv. Chim. Acta , 27 : 1748
   Google Scholar
• Szporny , L. and Gorog , P. 1961 . Biochem. Pharmacol. , 8 : 263
   Google Scholar
• Glaser , R. , Adin , I. , Shiftan , D. , Shi , Q. , Deutsh , H. M. , George , C. , Wu , K. M. and Froimowitz , M. 1998 . J. Org. Chem. , 63 : 1785 (a) For a very interesting paper on solution and solid-state conformational and structural analysis of N-methyl derivatives of methylphenidate, see
   Google Scholar
• Froimowitz , M. , Wu , K. M. , George , C. , VanDerveer , D. , Shi , Q. and Deutsch , H. M. 1998 . Structural Chemistry , 9 : 295 For crystal structures of analogs of threo-methylphenidate, see
   Google Scholar
• Maxwell , R. A. , Chaplin , E. , Eckhardt , S. B. , Soares , J. R. and Hite , G. 1970 . J. Pharmacol. Exp. Ther. , 173 : 158
   PubMed Web of Science ®Google Scholar
• Stinson , S. C. 1998 . Chemical & Engineering News , September 21 : 83
   Google Scholar
• Prashad , M. , Har , D. , Repic , O. , Blacklock , T. J. and Giannousis , P. 1998 . Tetrahedron:Asymmetry , 9 : 2133
   Web of Science ®Google Scholar
• The nomenclature assignment of threo and erythro for methylphenidate isomers is based on the relationship of the amine nitrogen to the carboxymethyl ester if the structures are drawn as Fisher projections with those substituents in the horizontal position. The carboxymethyl ester and amine nitrogen are on opposite sides for the threo isomers and on the same side for the erythro isomers.
   Google Scholar
• Fisher , M. J. and Overman , L. E. 1990 . J. Org. Chem. , 55 : 1447 α-ethoxy carbamate
   Google Scholar
• Tanaka , F. J. and Fuji , K. 1992 . Tetrahedron Lett. , 33 : 7885 Silyl ketene acetal: (a)
   Google Scholar
• Slougui , N. , Rousseau , G. and Conia , J. M. 1982 . Synthesis , : 58
   Google Scholar
• Pilli , R. A. , Dias , L. C. and Maldaner , A. O. 1995 . J. Org. Chem. , 60 : 717
   Google Scholar
• Pilli , R. A. , Dias , L. C. and Maldaner , A. O. 1993 . Tetrahedron Lett. , 34 : 2729
   Google Scholar